# EDGAR Filing Document

**Accession Number:** 0000771951
**File Stem:** 0000928816-23-000427
**Filing Date:** 2023-3
**Character Count:** 186523
**Document Hash:** fa744d8a854038578c55f7d4a936eddc
**Contains OCR:** False
**Source Format:** 

## Filing Content

## Filing Summary
**0000928816-23-000427.hdr.sgml**: 20230329

**ACCESSION NUMBER**: 0000928816-23-000427

**CONFORMED SUBMISSION TYPE**: N-CSRS

**PUBLIC DOCUMENT COUNT**: 20

**CONFORMED PERIOD OF REPORT**: 20230131

**FILED AS OF DATE**: 20230329

**DATE AS OF CHANGE**: 20230329

**EFFECTIVENESS DATE**: 20230329

**FILER**: 

**COMPANY DATA:**
- **COMPANY CONFORMED NAME:** PUTNAM TAX FREE INCOME TRUST
- **CENTRAL INDEX KEY:** 0000771951
- **IRS NUMBER:** 046483374
- **STATE OF INCORPORATION:** MA
- **FISCAL YEAR END:** 0731

**FILING VALUES:**
- **FORM TYPE:** N-CSRS
- **SEC ACT:** 1940 Act
- **SEC FILE NUMBER:** 811-04345
- **FILM NUMBER:** 23775071

**BUSINESS ADDRESS:**
- **STREET 1:** 100 FEDERAL STREET
- **CITY:** BOSTON
- **STATE:** MA
- **ZIP:** 02110
- **BUSINESS PHONE:** 6172921000

**MAIL ADDRESS:**
- **STREET 1:** 100 FEDERAL STREET
- **CITY:** BOSTON
- **STATE:** MA
- **ZIP:** 02110

**FORMER COMPANY:**
- **FORMER CONFORMED NAME:** PUTNAM TAX FREE INCOME TRUST /MA/
- **DATE OF NAME CHANGE:** 19920902

**FORMER COMPANY:**
- **FORMER CONFORMED NAME:** PUTNAM TAX FREE INCOME TRUST
- **DATE OF NAME CHANGE:** 19920101

## Series and Classes Contracts Data

### Putnam Tax-Free High Yield Fund (Series ID: S000003861)

| Class ID   | Class Name      | Ticker Symbol   |
|:---|:---|:---|
| C000010821 | Class C Shares  |  |
| C000010822 | Class A Shares  | PTHAX           |
| C000010823 | Class B Shares  | PTHYX           |
| C000060536 | CLASS Y         |  |
| C000202841 | Class R6 Shares |  |

UNITED STATES<br>SECURITIES AND EXCHANGE COMMISSION

Washington, D.C. 20549

<br>**FORM N-CSR**<br>

**CERTIFIED SHAREHOLDER REPORT OF REGISTERED<br>MANAGEMENT INVESTMENT COMPANIES**<br>

Investment Company Act file number: (811-04345)

Exact name of registrant as specified in charter: Putnam Tax Free Income Trust

Address of principal executive offices: 100 Federal Street, Boston, Massachusetts 02110

Name and address of agent for service: Stephen Tate, Vice President<br>100 Federal Street<br>Boston, Massachusetts 02110

Copy to: Bryan Chegwidden, Esq.<br>Ropes & Gray LLP<br>1211 Avenue of the Americas<br>New York, New York 10036

Registrant's telephone number, including area code: (617) 292-1000

Date of fiscal year end: July 31, 2023

Date of reporting period: August 1, 2022 – January 31, 2023

<br><u>Item 1. Report to Stockholders:</u>

The following is a copy of the report transmitted to stockholders pursuant to Rule 30e-1 under the Investment Company Act of 1940:

![](taxfreehighyieldx1x1.jpg) <br>

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Putnam<br>Tax-Free High Yield<br>Fund

**Semiannual report**<br>**1** \| **31** \| **23**

---

| | |
|:---|:---|
| [Message from the Trustees](#page_3) | [1](#page_3) |
| [About the fund](#page_4) | [2](#page_4) |
| [Interview with your fund's portfolio manager](#page_7) | [5](#page_7) |
| [Your fund's performance](#page_11) | [9](#page_11) |
| [Your fund's expenses](#yfe) | [11](#yfe) |
| [Consider these risks before investing](#page_15) | [13](#page_15) |
| [Terms and definitions](#page_16) | [14](#page_16) |
| [Other information for shareholders](#page_18) | [16](#page_18) |
| [Financial statements](#page_19) | [17](#page_19) |

---

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**Message from the Trustees**

March 9, 2023

Dear Fellow Shareholder:

Stock and bond markets rose in early 2023 as inflation continued to ease and the U.S. Federal Reserve moderated its interest-rate increases. Investors showed optimism that the Fed might slow the economy and reduce inflation without causing a recession. Still, caution may be warranted. While the Fed has reduced the size of its interest-rate increases, it also signaled that more rate hikes are likely if concerns persist about a resurgence in inflation.

Putnam's investment teams believe a recession is possible this year or next. However, they also are finding what they believe to be attractive investment opportunities in a range of asset classes, including stocks and taxable and tax-exempt bonds. As active researchers, our teams analyze interest-rate and credit risks as they seek out investments for your fund. They also consider how stocks and bonds are likely to perform in uncertain economic conditions.

Thank you for investing with Putnam. ![](taxfreehighyieldx3x1.jpg) <br>

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![](taxfreehighyieldx4x1.jpg) <br>

Taxes can take a bite out of the distributions from fixed income securities. Putnam Tax-Free High Yield Fund can help reduce the impact of both by investing in higher-yielding, lower-rated municipal bonds that are exempt from federal and state income taxes.

**Meticulous credit research**

Municipal bonds finance important public projects, such as schools, roads, and hospitals, and they can help investors keep more of the income they receive from their investment. Members of Putnam's fixed income organization have a range of skills to analyze the credit risk of below-investment-grade municipal bonds and help build a well-diversified portfolio.

![](taxfreehighyieldx4x2.jpg) <br>

2 Tax-Free High Yield Fund

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![](taxfreehighyieldx5x1.jpg) <br>

**The bottom line: Income you keep after paying taxes matters more than pre-tax yield.**

You keep more income from municipal bonds because it is exempt from most state and federal income taxes. ![](taxfreehighyieldx5x2.jpg) <br>

Sources: Putnam, Bloomberg Index Services Limited, as of 1/31/23. Past performance is no guarantee of future results. Yields for U.S. Treasuries, investment-grade corporates, and municipal bonds are represented by the average "yield to worst" — a calculation of the lowest possible yield generated without defaulting — of the Bloomberg U.S. Treasury Index, an unmanaged index of U.S. dollar-denominated, fixed-rate, nominal debt issued by the U.S. Treasury; the Bloomberg U.S. Corporate Bond Index, an unmanaged index of U.S. dollar-denominated, investment-grade, fixed-rate, taxable corporate bonds; and the Bloomberg Municipal Bond Index, an unmanaged index of long-term, fixed-rate, investment-grade tax-exempt bonds, respectively. You cannot invest directly in an index. Bond investments are subject to interest-rate risk (the risk of bond prices falling if interest rates rise) and credit risk (the risk of an issuer defaulting on interest or principal payments). Interest-rate risk is greater for longer-term bonds, and credit risk is greater for below-investment-grade bonds. Income from municipal bonds may be subject to the alternative minimum tax. Annual after-tax income is based on a 40.80% federal income tax rate. This rate reflects the Tax Cuts and Jobs Act of 2017 and includes the 3.80% Medicare surtax. The income data is based on a hypothetical $100,000 investment. ![](taxfreehighyieldx5x3.jpg) <br>

Source: Moody's Investors Service, Annual U.S. Municipal Bond Defaults and Recoveries, Five-Year Average Cumulative Default Rates, 1970–2021 (April 2022). Most recent data available.

Tax-Free High Yield Fund 3

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![](taxfreehighyieldx6x1.jpg) <br>

*Current performance may be lower or higher than the quoted past performance, which cannot guarantee future results. Share price, principal value, and return will fluctuate, and you may have a gain or a loss when you sell your shares. Performance of class A shares assumes reinvestment of distributions and does not account for taxes. Fund returns in the bar chart do not reflect a sales charge of 4.00%; had they, returns would have been lower. Performance for class A shares before their inception (9/20/93) is derived from the historical performance of class B shares. See below and pages 9–11 for additional performance information. For a portion of the periods, the fund had expense limitations, without which returns would have been lower. To obtain the most recent month-end performance, visit putnam.com.*

*Returns for periods of less than one year are not annualized.*

*All Bloomberg indices are provided by Bloomberg Index Services Limited.*

*Lipper peer group median is provided by Lipper, a Refinitiv company.* ![](taxfreehighyieldx6x2.jpg) <br>

This comparison shows your fund's performance in the context of broad market indexes for the six months ended 1/31/23. See above and pages 9–11 for additional fund performance information. Index descriptions can be found on pages 14–15.

All Bloomberg indices are provided by Bloomberg Index Services Limited.

4 Tax-Free High Yield Fund

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![](taxfreehighyieldx7x1.jpg) <br> ![](taxfreehighyieldx7x2.jpg) <br>

**Paul, how was the market environment for municipal bonds during the six-month period ended January 31, 2023?**

After a challenging first few months, municipal bonds regained their footing. November 2022 was especially strong for the asset class, despite the Federal Reserve's announcement of its fourth consecutive 0.75% interest-rate increase on November 3. Investors were heartened to see that the Consumer Price Index [CPI], a widely used measure of inflation, came in better than expected at 7.7% for October 2022. Investors interpreted this as evidence that the Fed was making progress in subduing stubbornly high prices. As the month ended, the Fed hinted it might temper the degree of interest-rate hikes as early as December 2022.

The CPI for November also showed progress, with year-over-year inflation falling to 7.1%. It was the smallest 12-month increase since December 2021. In our view, this gave the Fed room to raise its benchmark interest rate by only half a percentage point on December 15, 2022. However, Fed policymakers also signaled the fight against inflation was not over. Fed Chair Jerome Powell stated that "it will take substantially more evidence to give confidence that inflation is on a sustained downward path."

Tax-Free High Yield Fund 5

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![](taxfreehighyieldx8x1.jpg) <br>

Allocations are shown as a percentage of the fund's net assets as of 1/31/23. Cash and net other assets, if any, represent the market value weights of cash, derivatives, short-term securities, and other unclassified assets in the portfolio. Summary information may differ from the information in the portfolio schedule notes included in the financial statements due to the inclusion of derivative securities, any interest accruals, the timing of matured security transactions, the use of different classifications of securities for presentation purposes, and rounding. Holdings and allocations may vary over time. ![](taxfreehighyieldx8x2.jpg) <br>

Credit qualities are shown as a percentage of the fund's net assets as of 1/31/23. A bond rated BBB or higher (SP-3 or higher, for short-term debt) is considered investment grade. This chart reflects the highest security rating provided by one or more of Standard & Poor's, Moody's, and Fitch. Ratings may vary over time.

Cash and net other assets, if any, represent the market value weights of cash, derivatives, and short-term securities in the portfolio. The fund itself has not been rated by an independent rating agency.

6 Tax-Free High Yield Fund

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Minutes from the central bank's policy meeting in December revealed that Fed officials agreed it would be appropriate to slow the pace of its aggressive rate hikes to minimize the risks to economic growth. At period-end, the Fed raised its benchmark rate by 0.25%, elevating its benchmark interest rate to a target range of 4.50%–4.75%.

Market technicals improved during the period as well. Demand rebounded amid the improvement in market sentiment. At the same time, new issue supply was well below average due to the sharp rise in interest rates. This imbalance aided returns. With these positive developments, November 2022's return of 4.68% represented the strongest monthly return for the Bloomberg Municipal Bond Index [the fund's benchmark] since 1986.

For the six months ended January 31, 2023, the fund's benchmark returned 0.73%. Intermediate-term municipal bonds outperformed longer-term and shorter-term cohorts. From a credit perspective, investment-grade municipal bonds performed better than higher-yielding, lower-rated bonds, which aided our positioning.

**What is your current assessment of the health of the municipal bond market?**

Municipal credit fundamentals continue to be stable, in our view. Higher employment and increasing wages have bolstered tax receipts. Home values, a factor in property tax revenues, have been facing headwinds in the form of rising mortgage rates. We believe assessed values, another factor in taxes, should continue to reflect growth given the roughly two-year lag between tax assessments and actual property values.

State and local tax collections were up 16% year over year through the third quarter of 2022 compared with the same period in 2021 [most recent data available]. Unprecedented fiscal support during the Covid-19 pandemic, as well as strong economic growth during the second half of 2020 and 2021, put most state and local governments in their best fiscal shape in more than a decade, in our view. Municipal defaults are running near long-term averages as of January 31, 2023, and they remain a very small percentage of the market. As such, we believe the credit outlook remains favorable, though we continue to actively monitor the market. We expect economic conditions to slow during 2023, which could impact municipal bond credit quality, in our view.

![](taxfreehighyieldx9x1.jpg)

**How did the fund perform during the period?**

For the six months ended January 31, 2023, the fund's class A shares underperformed the higher-quality benchmark but outperformed the median return of its Lipper peer group, High Yield Municipal Debt Funds.

**What strategies or holdings influenced the fund's performance during the reporting period?**

At period-end, the fund held an overweight exposure to lower-investment-grade bonds and those rated BBB+ and BB relative to the benchmark. We remain cautious on lower-rated municipal bonds in general, given our view that the Fed's aggressive tightening cycle could result in slower U.S. economic growth in 2023. However, we have found value in some of the upper tiers of the high-yield market. While credit spreads widened over the period, they were not excessively wide versus previous recessionary periods, in our view.

The fund was invested in a wide range of sectors, including land-secured, charter school, and long-term-care bonds. Duration positioning, a measure of the fund's interest-rate sensitivity, was slightly long relative to the average level of its Lipper peer group. We believe this positioning may help the fund outperform its peers if the steep rise in bond yields reverses course.

The fund remained underweight in its exposure to Puerto Rico municipal debt relative to its Lipper peer group. However, we note that

Tax-Free High Yield Fund 7

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the U.S. territory has experienced recent improvement in credit fundamentals since coming out of bankruptcy in March 2022, in our view. We continue to closely monitor Puerto Rico's credit fundamentals and remain vigilant for investment opportunities.

**What do you see on the horizon that could influence your management of the fund?**

With the 6.5% CPI reading for December 2022, the Fed raised its benchmark rate by just a quarter percentage point as the reporting period closed. While it appears to us that inflation has peaked in this cycle, we believe U.S. economic data remains relatively strong. Especially noteworthy is the low U.S. unemployment rate and strong consumer spending. We presume this will keep the Fed on track to continue ratcheting up interest rates to slow economic growth and the jobs market. That said, we think the bulk of the tightening is behind us and Fed monetary policy is set to enter the fine-tuning stage of the cycle. Market expectations are for the Fed to complete its tightening cycle by the summer of 2023.

Seasonal factors are typically weaker in late winter and early spring but turn more favorable in late spring and summer months. Against this backdrop, we believe valuations offer investors attractive tax-free income, as well as the potential for price appreciation once the Fed concludes its monetary tightening cycle.

**Thank you, Paul, for your time and insights today.**

*The views expressed in this report are exclusively those of Putnam Management and are subject to change. They are not meant as investment advice. Please note that the holdings discussed in this report may not have been held by the fund for the entire period.*

*Portfolio composition is subject to review in accordance with the fund's investment strategy and may vary in the future. Current and future portfolio holdings are subject to risk. Statements in the Q&A concerning the fund's performance or portfolio composition relative to those of the fund's Lipper peer group may reference information produced by Lipper Inc. or through a third party.* ![](taxfreehighyieldx10x1.jpg) <br>

This chart shows how the fund's top weightings have changed over the past six months. Allocations are shown as a percentage of the fund's net assets. Current period summary information may differ from the information in the portfolio schedule notes included in the financial statements due to the inclusion of derivative securities, any interest accruals, the timing of matured security transactions, the use of different classifications of securities for presentation purposes, and rounding. Holdings and allocations may vary over time.

8 Tax-Free High Yield Fund

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**Your fund's performance**

This section shows your fund's performance, price, and distribution information for periods ended January 31, 2023, the end of the first half of its current fiscal year. In accordance with regulatory requirements for mutual funds, we also include performance information as of the most recent calendar quarter-end and expense information taken from the fund's current prospectus. Performance should always be considered in light of a fund's investment strategy. Data represent past performance. Past performance does not guarantee future results. More recent returns may be less or more than those shown. Investment return and principal value will fluctuate, and you may have a gain or a loss when you sell your shares. Performance information does not reflect any deduction for taxes a shareholder may owe on fund distributions or on the redemption of fund shares. For the most recent month-end performance, please visit the Individual Investors section at putnam.com or call Putnam at 1-800-225-1581. Class R6 and Y shares are not available to all investors. See the Terms and definitions section in this report for definitions of the share classes offered by your fund.

**Annualized fund performance** Total return for periods ended 1/31/23

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| | | | | | | |
|:---|:---|:---|:---|:---|:---|:---|
|  | **Life of fund** | **10 years** | **5 years** | **3 years** | **1 year** | **6 months** |
| **Class A** (9/20/93) |  |  |  |  |  |  |
| Before sales charge | 5.51% | 2.98% | 2.16% | –0.69% | –6.43% | –0.35% |
| After sales charge | 5.40 | 2.56 | 1.33 | –2.04 | –10.17 | –4.34 |
| **Class B** (9/9/85) |  |  |  |  |  |  |
| Before CDSC | 5.51 | 2.48 | 1.53 | –1.29 | –7.03 | –0.74 |
| After CDSC | 5.51 | 2.48 | 1.19 | –2.20 | –11.55 | –5.62 |
| **Class C** (2/1/99) |  |  |  |  |  |  |
| Before CDSC | 5.33 | 2.35 | 1.38 | –1.44 | –7.16 | –0.81 |
| After CDSC | 5.33 | 2.35 | 1.38 | –1.44 | –8.06 | –1.79 |
| **Class R6** (5/22/18) |  |  |  |  |  |  |
| Net asset value | 5.38 | 3.25 | 2.43 | –0.42 | –6.15 | –0.21 |
| **Class Y** (1/2/08) |  |  |  |  |  |  |
| Net asset value | 5.38 | 3.23 | 2.41 | –0.46 | –6.23 | –0.30 |

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Current performance may be lower or higher than the quoted past performance, which cannot guarantee future results. After-sales-charge returns for class A shares reflect the deduction of the maximum 4.00% sales charge levied at the time of purchase. Class B share returns after contingent deferred sales charge (CDSC) reflect the applicable CDSC, which is 5% in the first year, declining over time to 1% in the sixth year, and is eliminated thereafter. Class C share returns after CDSC reflect a 1% CDSC for the first year that is eliminated thereafter. Class R6 and Y shares have no initial sales charge or CDSC. Performance for class A, C, and Y shares before their inception is derived from the historical performance of class B shares, adjusted for the applicable sales charge (or CDSC) and, for class C shares, the higher operating expenses for such shares. Performance for class R6 shares prior to their inception is derived from the historical performance of class Y shares and has not been adjusted for the lower investor servicing fees applicable to class R6 shares; had it, returns would have been higher.

Returns for periods of less than one year are not annualized.

For a portion of the periods, the fund had expense limitations, without which returns would have been lower.

Class B and C share performance reflects conversion to class A shares after eight years.

Tax-Free High Yield Fund 9

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**Comparative annualized index returns** For periods ended 1/31/23

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| | | | | | | |
|:---|:---|:---|:---|:---|:---|:---|
|  | **Life of fund** | **10 years** | **5 years** | **3 years** | **1 year** | **6 months** |
| **Bloomberg Municipal** |  |  |  |  |  |  |
| **Bond Index** | 5.85% | 2.38% | 2.07% | –0.42% | –3.25% | 0.73% |
| **Lipper High Yield** |  |  |  |  |  |  |
| **Municipal Debt Funds** |  |  |  |  |  |  |
| **category median**<sup>\*</sup> | 4.37 | 2.78 | 1.73 | –1.25 | –8.04 | –1.24 |

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Index and Lipper results should be compared with fund performance before sales charge, before CDSC, or at net asset value.

Returns for periods of less than one year are not annualized.

All Bloomberg indices are provided by Bloomberg Index Services Limited.

Lipper peer group median is provided by Lipper, a Refinitiv company.

<sup>\*</sup> Over the 6-month, 1-year, 3-year, 5-year, 10-year, and life-of-fund periods ended 1/31/23, there were 192, 191, 185, 166, 106, and 13 funds, respectively, in this Lipper category.

**Fund price and distribution information** For the six-month period ended 1/31/23

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| | | | | | | |
|:---|:---|:---|:---|:---|:---|:---|
| **Distributions** | **Class A** | **Class A** | **Class B** | **Class C** | **Class R6** | **Class Y** |
| Number | 6 | 6 | 6 | 6 | 6 | 6 |
| Income<sup>1</sup> | $0.208156 | $0.208156 | $0.174800 | $0.166650 | $0.224122 | $0.223141 |
| Capital gains<sup>2</sup> |  |  |  |  |  |  |
| **Total** | **$0.208156** | **$0.208156** | **$0.174800** | **$0.166650** | **$0.224122** | **$0.223141** |
|  | Before | After | Net | Net | Net | Net |
|  | sales | sales | asset | asset | asset | asset |
| **Share value** | charge | charge | value | value | value | value |
| 7/31/22 | $11.70 | $12.19 | $11.74 | $11.74 | $11.76 | $11.76 |
| 1/31/23 | 11.44 | 11.92 | 11.47 | 11.47 | 11.50 | 11.49 |
|  | Before | After | Net | Net | Net | Net |
| **Current rate** | sales | sales | asset | asset | asset | asset |
| **(end of period)** | charge | charge | value | value | value | value |
| Current dividend rate<sup>3</sup> | 3.48% | 3.34% | 2.89% | 2.74% | 3.75% | 3.73% |
| Taxable equivalent<sup>4</sup> | 5.88 | 5.64 | 4.88 | 4.63 | 6.33 | 6.30 |
| Current 30-day |  |  |  |  |  |  |
| SEC yield<sup>5</sup> | N/A | 3.68 | 3.18 | 3.03 | 4.04 | 4.02 |
| Taxable equivalent<sup>4</sup> | N/A | 6.22 | 5.37 | 5.12 | 6.82 | 6.79 |

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The classification of distributions, if any, is an estimate. Before-sales-charge share value and current dividend rate for class A shares, if applicable, do not take into account any sales charge levied at the time of purchase. After-sales-charge share value, current dividend rate, and current 30-day SEC yield, if applicable, are calculated assuming that the maximum sales charge (4.00% for class A shares) was levied at the time of purchase. Final distribution information will appear on your year-end tax forms.

<sup>1</sup> For some investors, investment income may be subject to the federal alternative minimum tax.

<sup>2</sup> Capital gains, if any, are taxable for federal and, in most cases, state purposes.

<sup>3</sup> Most recent distribution, including any return of capital and excluding capital gains, annualized and divided by share price before or after sales charge at period-end.

<sup>4</sup> Assumes maximum 40.80% federal tax rate for 2023. Results for investors subject to lower tax rates would not be as advantageous.

<sup>5</sup> Based only on investment income and calculated using the maximum offering price for each share class, in accordance with SEC guidelines.

10 Tax-Free High Yield Fund

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**Annualized fund performance as of most recent calendar quarter**<br>Total return for periods ended 12/31/22

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| | | | | | | |
|:---|:---|:---|:---|:---|:---|:---|
|  | **Life of fund** | **10 years** | **5 years** | **3 years** | **1 year** | **6 months** |
| **Class A** (9/20/93) |  |  |  |  |  |  |
| Before sales charge | 5.40% | 2.63% | 1.12% | –1.52% | –12.80% | –0.62% |
| After sales charge | 5.28 | 2.21 | 0.30 | –2.85 | –16.29 | –4.60 |
| **Class B** (9/9/85) |  |  |  |  |  |  |
| Before CDSC | 5.40 | 2.12 | 0.50 | –2.12 | –13.34 | –0.94 |
| After CDSC | 5.40 | 2.12 | 0.16 | –3.02 | –17.55 | –5.82 |
| **Class C** (2/1/99) |  |  |  |  |  |  |
| Before CDSC | 5.22 | 2.00 | 0.37 | –2.23 | –13.38 | –0.99 |
| After CDSC | 5.22 | 2.00 | 0.37 | –2.23 | –14.22 | –1.97 |
| **Class R6** (5/22/18) |  |  |  |  |  |  |
| Net asset value | 5.27 | 2.89 | 1.37 | –1.24 | –12.51 | –0.49 |
| **Class Y** (1/2/08) |  |  |  |  |  |  |
| Net asset value | 5.27 | 2.87 | 1.35 | –1.28 | –12.59 | –0.57 |

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See the discussion following the fund performance table on page 9 for information about the calculation of fund performance.

Returns for periods of less than one year are not annualized.

**<br>Your fund's expenses**

As a mutual fund investor, you pay ongoing expenses, such as management fees, distribution fees (12b-1 fees), and other expenses. Using the following information, you can estimate how these expenses affect your investment and compare them with the expenses of other funds. You may also pay one-time transaction expenses, including sales charges (loads) and redemption fees, which are not shown in this section and would have resulted in higher total expenses. For more information, see your fund's prospectus or talk to your financial representative.

**Expense ratios**

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| | | | | | |
|:---|:---|:---|:---|:---|:---|
|  | **Class A** | **Class B** | **Class C** | **Class R6** | **Class Y** |
| Total annual operating expenses for the fiscal |  |  |  |  |  |
| year ended 7/31/22 | 0.87% | 1.47% | 1.62% | 0.60% | 0.62% |
| Annualized expense ratio for the six-month |  |  |  |  |  |
| period ended 1/31/23<sup>\*</sup> | 1.00% | 1.60% | 1.75% | 0.72% | 0.75% |

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Fiscal year expense information in this table is taken from the most recent prospectus, is subject to change, and may differ from that shown for the annualized expense ratio and in the financial highlights of this report.

Expenses are shown as a percentage of average net assets.

<sup>\*</sup> Expense ratios for each class are for the fund's most recent fiscal half year. As a result of this, ratios may differ from expense ratios based on one-year data in the financial highlights.

Tax-Free High Yield Fund 11

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**Expenses per $1,000**

The following table shows the expenses you would have paid on a $1,000 investment in each class of the fund from 8/1/22 to 1/31/23. It also shows how much a $1,000 investment would be worth at the close of the period, assuming *actual returns* and expenses.

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| | | | | | |
|:---|:---|:---|:---|:---|:---|
|  | **Class A** | **Class B** | **Class C** | **Class R6** | **Class Y** |
| Expenses paid per $1,000<sup>\*†</sup> | $5.03 | $8.04 | $8.79 | $3.63 | $3.78 |
| Ending value (after expenses) | $996.50 | $992.60 | $991.90 | $997.90 | $997.00 |

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<sup>\*</sup> Expenses for each share class are calculated using the fund's annualized expense ratio for each class, which represents the ongoing expenses as a percentage of average net assets for the six months ended 1/31/23. The expense ratio may differ for each share class.

<sup>†</sup> Expenses are calculated by multiplying the expense ratio by the average account value for the period; then multiplying the result by the number of days in the period (184); and then dividing that result by the number of days in the year (365).

**Estimate the expenses you paid**

To estimate the ongoing expenses you paid for the six months ended 1/31/23, use the following calculation method. To find the value of your investment on 8/1/22, call Putnam at 1-800-225-1581. ![](taxfreehighyieldx14x1.jpg) <br>

**Compare expenses using the SEC's method**

The Securities and Exchange Commission (SEC) has established guidelines to help investors assess fund expenses. Per these guidelines, the following table shows your fund's expenses based on a $1,000 investment, assuming a *hypothetical 5% annualized return*. You can use this information to compare the ongoing expenses (but not transaction expenses or total costs) of investing in the fund with those of other funds. All mutual fund shareholder reports will provide this information to help you make this comparison. Please note that you cannot use this information to estimate your actual ending account balance and expenses paid during the period.

---

| | | | | | |
|:---|:---|:---|:---|:---|:---|
|  | **Class A** | **Class B** | **Class C** | **Class R6** | **Class Y** |
| Expenses paid per $1,000<sup>\*†</sup> | $5.09 | $8.13 | $8.89 | $3.67 | $3.82 |
| Ending value (after expenses) | $1020.16 | $1017.14 | $1016.38 | $1021.58 | $1021.42 |

---

<sup>\*</sup> Expenses for each share class are calculated using the fund's annualized expense ratio for each class, which represents the ongoing expenses as a percentage of average net assets for the six months ended 1/31/23. The expense ratio may differ for each share class.

<sup>†</sup> Expenses are calculated by multiplying the expense ratio by the average account value for the six-month period; then multiplying the result by the number of days in the six-month period (184); and then dividing that result by the number of days in the year (365).

12 Tax-Free High Yield Fund

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**Consider these risks before investing**

Capital gains, if any, are taxed at the federal and, in most cases, state levels. For some investors, investment income may be subject to the federal alternative minimum tax. Income from federally tax-exempt funds may be subject to state and local taxes.

Bond investments are subject to interest-rate risk (the risk of bond prices falling if interest rates rise) and credit risk (the risk of an issuer defaulting on interest or principal payments). Bond investments may be more susceptible to downgrades or defaults during economic downturns or other periods of economic stress. Interest-rate risk is generally greater for longer-term bonds, and credit risk is generally greater for below-investment-grade bonds. Unlike bonds, funds that invest in bonds have fees and expenses. The fund may invest significantly in particular segments of the tax-exempt debt market, making it more vulnerable to fluctuations in the values of the securities it holds than a more broadly invested fund. Interest the fund receives might be taxable.

The value of investments in the fund's portfolio may fall or fail to rise over extended periods of time for a variety of reasons, including general economic, political, or financial market conditions; investor sentiment and market perceptions; government actions; geopolitical events or changes; and factors related to a specific issuer, geography, industry, or sector. These and other factors may lead to increased volatility and reduced liquidity in the fund's portfolio holdings.

Our investment techniques, analyses, and judgments may not produce the outcome we intend. The investments we select for the fund may not perform as well as other securities that we do not select for the fund. We, or the fund's other service providers, may experience disruptions or operating errors that could negatively impact the fund. You can lose money by investing in the fund.

Tax-Free High Yield Fund 13

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**Terms and definitions**

**Important terms**

**Total return** shows how the value of the fund's shares changed over time, assuming you held the shares through the entire period and reinvested all distributions in the fund.

**Before sales charge,** or net asset value, is the price, or value, of one share of a mutual fund, without a sales charge. Before-sales-charge figures fluctuate with market conditions. They are calculated by dividing the net assets of each class of shares by the number of outstanding shares in the class.

**After sales charge** is the price of a mutual fund share plus the maximum sales charge levied at the time of purchase. After-sales-charge performance figures shown here assume the 4.00% maximum sales charge for class A shares.

**Contingent deferred sales charge (CDSC)** is generally a charge applied at the time of the redemption of class B or C shares and assumes redemption at the end of the period. Your fund's class B CDSC declines over time from a 5% maximum during the first year to 1% during the sixth year. After the sixth year, the CDSC no longer applies. The CDSC for class C shares is 1% for one year after purchase.

**Share classes**

**Class A shares** are generally subject to an initial sales charge and no CDSC (except on certain redemptions of shares bought without an initial sales charge).

**Class B shares** are closed to new investments and are only available by exchange from class B shares of another Putnam fund or through dividend and/or capital gains reinvestment. They are not subject to an initial sales charge and may be subject to a CDSC.

**Class C shares** are not subject to an initial sales charge and are subject to a CDSC only if the shares are redeemed during the first year.

**Class R6 shares** are not subject to an initial sales charge or CDSC and carry no 12b-1 fee. They are generally only available to employer-sponsored retirement plans, corporate and institutional clients, and clients in other approved programs.

**Class Y shares** are not subject to an initial sales charge or CDSC and carry no 12b-1 fee. They are generally only available to corporate and institutional clients and clients in other approved programs.

**Fixed income terms**

**Current rate** is the annual rate of return earned from dividends or interest of an investment. Current rate is expressed as a percentage of the price of a security, fund share, or principal investment.

**Yield curve** is a graph that plots the yields of bonds with equal credit quality against their differing maturity dates, ranging from shortest to longest. It is used as a benchmark for other debt, such as mortgage or bank lending rates.

**Comparative indexes**

**Bloomberg Municipal Bond Index** is an unmanaged index of long-term, fixed-rate, investment-grade tax-exempt bonds.

**Bloomberg U.S. Aggregate Bond Index** is an unmanaged index of U.S. investment-grade fixed income securities.

**ICE BofA (Intercontinental Exchange Bank of America) U.S. 3-Month Treasury Bill Index** is an unmanaged index that seeks to measure the performance of U.S. Treasury bills available in the marketplace.

**S&P 500**<sup>®</sup> **Index** is an unmanaged index of common stock performance.

Indexes assume reinvestment of all distributions and do not account for fees. Securities and performance of a fund and an index will differ. You cannot invest directly in an index.

14 Tax-Free High Yield Fund

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BLOOMBERG<sup>®</sup> is a trademark and service mark of Bloomberg Finance L.P. and its affiliates (collectively "Bloomberg"). Bloomberg or Bloomberg's licensors own all proprietary rights in the Bloomberg Indices. Neither Bloomberg nor Bloomberg's licensors approve or endorse this material, or guarantee the accuracy or completeness of any information herein, or make any warranty, express or implied, as to the results to be obtained therefrom, and to the maximum extent allowed by law, neither shall have any liability or responsibility for injury or damages arising in connection therewith.

ICE Data Indices, LLC ("ICE BofA"), used with permission. ICE BofA permits use of the ICE BofA indices and related data on an "as is" basis; makes no warranties regarding same; does not guarantee the suitability, quality, accuracy, timeliness, and/or completeness of the ICE BofA indices or any data included in, related to, or derived therefrom; assumes no liability in connection with the use of the foregoing; and does not sponsor, endorse, or recommend Putnam Investments, or any of its products or services.

**Lipper,** a Refinitiv company, is a third-party industry-ranking entity that ranks mutual funds. Its rankings do not reflect sales charges. Lipper rankings are based on total return at net asset value relative to other funds that have similar current investment styles or objectives as determined by Lipper. Lipper may change a fund's category assignment at its discretion. Lipper category medians reflect performance trends for funds within a category.

Tax-Free High Yield Fund 15

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**Other information for shareholders**

**Important notice regarding delivery of shareholder documents**

In accordance with Securities and Exchange Commission (SEC) regulations, Putnam sends a single notice of internet availability, or a single printed copy, of annual and semiannual shareholder reports, prospectuses, and proxy statements to Putnam shareholders who share the same address, unless a shareholder requests otherwise. If you prefer to receive your own copy of these documents, please call Putnam at 1-800-225-1581, and Putnam will begin sending individual copies within 30 days.

**Proxy voting**

Putnam is committed to managing our mutual funds in the best interests of our shareholders. The Putnam funds' proxy voting guidelines and procedures, as well as information regarding how your fund voted proxies relating to portfolio securities during the 12-month period ended June 30, 2022, are available in the Individual Investors section of putnam.com and on the SEC's website, www.sec.gov. If you have questions about finding forms on the SEC's website, you may call the SEC at 1-800-SEC-0330. You may also obtain the Putnam funds' proxy voting guidelines and procedures at no charge by calling Putnam's Shareholder Services at 1-800-225-1581.

**Fund portfolio holdings**

The fund will file a complete schedule of its portfolio holdings with the SEC for the first and third quarters of each fiscal year on Form N-PORT within 60 days of the end of such fiscal quarter. Shareholders may obtain the fund's Form N-PORT on the SEC's website at www.sec.gov.

Prior to its use of Form N-PORT, the fund filed its complete schedule of its portfolio holdings with the SEC on Form N-Q, which is available online at www.sec.gov.

**Trustee and employee fund ownership**

Putnam employees and members of the Board of Trustees place their faith, confidence, and, most importantly, investment dollars in Putnam mutual funds. As of January 31, 2023, Putnam employees had approximately $478,000,000 and the Trustees had approximately $64,000,000 invested in Putnam mutual funds. These amounts include investments by the Trustees' and employees' immediate family members as well as investments through retirement and deferred compensation plans.

16 Tax-Free High Yield Fund

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**Financial statements**

**These sections of the report, as well as the accompanying Notes, constitute the fund's financial statements.**

**The fund's portfolio** lists all the fund's investments and their values as of the last day of the reporting period. Holdings are organized by asset type and industry sector, country, or state to show areas of concentration and diversification.

**Statement of assets and liabilities** shows how the fund's net assets and share price are determined. All investment and non-investment assets are added together. Any unpaid expenses and other liabilities are subtracted from this total. The result is divided by the number of shares to determine the net asset value per share, which is calculated separately for each class of shares. (For funds with preferred shares, the amount subtracted from total assets includes the liquidation preference of preferred shares.)

**Statement of operations** shows the fund's net investment gain or loss. This is done by first adding up all the fund's earnings — from dividends and interest income — and subtracting its operating expenses to determine net investment income (or loss). Then, any net gain or loss the fund realized on the sales of its holdings — as well as any unrealized gains or losses over the period — is added to or subtracted from the net investment result to determine the fund's net gain or loss for the fiscal period.

**Statement of changes in net assets** shows how the fund's net assets were affected by the fund's net investment gain or loss, by distributions to shareholders, and by changes in the number of the fund's shares. It lists distributions and their sources (net investment income or realized capital gains) over the current reporting period and the most recent fiscal year-end. The distributions listed here may not match the sources listed in the Statement of operations because the distributions are determined on a tax basis and may be paid in a different period from the one in which they were earned. Dividend sources are estimated at the time of declaration. Actual results may vary. Any non-taxable return of capital cannot be determined until final tax calculations are completed after the end of the fund's fiscal period.

**Financial highlights** provide an overview of the fund's investment results, per-share distributions, expense ratios, net investment income ratios, and portfolio turnover in one summary table, reflecting the five most recent reporting periods. In a semiannual report, the highlights table also includes the current reporting period.

Tax-Free High Yield Fund 17

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**The fund's portfolio** 1/31/23 (Unaudited)

**Key to holding's abbreviations**

---

| |
|:---|
| **AGM** Assured Guaranty Municipal Corporation |
| **AMBAC** AMBAC Indemnity Corporation |
| **BAM** Build America Mutual |
| **COP** Certificates of Participation |
| **G.O. Bonds** General Obligation Bonds |
| **U.S. Govt. Coll.** U.S. Government Collateralized |
| **VRDN** Variable Rate Demand Notes, which are floating-rate securities with long-term maturities that carry coupons that reset and are payable upon demand either daily, weekly or monthly. The rate shown is the current interest rate at the close of the reporting period. Rates are set by remarketing agents and may take into consideration market supply and demand, credit quality and the current SIFMA Municipal Swap Index rate, which was 1.66% as of the close of the reporting period. |

---

---

| | | | |
|:---|:---|:---|:---|
| **MUNICIPAL BONDS AND NOTES (102.9%)\*** | **Rating\*\*** | **Principal amount** | **Value** |
| **Alabama (1.7%)** | **Alabama (1.7%)** | **Alabama (1.7%)** | **Alabama (1.7%)** |
| Jefferson Cnty., Swr. Rev. Bonds |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;Ser. D, 6.50%, 10/1/53 | BBB | $3000000 | $3207682 |
| &nbsp;&nbsp;&nbsp;&nbsp;stepped-coupon zero % (7.750%, 10/1/23), 10/1/46 <sup>††</sup> | BBB | 8800000 | 9030864 |
|  |  |  | **12238546** |
| **Alaska (1.2%)** | **Alaska (1.2%)** | **Alaska (1.2%)** | **Alaska (1.2%)** |
| AK State Indl. Dev. & Export Auth. Rev. Bonds, (Tanana Chiefs Conference), Ser. A, 4.00%, 10/1/49 | A+/F | 8500000 | 8184570 |
|  |  |  | **8184570** |
| **Arizona (3.5%)** | **Arizona (3.5%)** | **Arizona (3.5%)** | **Arizona (3.5%)** |
| AZ State Indl. Dev. Auth. Charter School Rev. Bonds, (Equitable School Revolving Fund, LLC), 4.00%, 11/1/51 | A | 1000000 | 901322 |
| AZ State Indl. Dev. Auth. Ed. Rev. Bonds, (KIPP New York, Inc., Jerome Fac.), Ser. B, 4.00%, 7/1/51 | BBB- | 2000000 | 1708146 |
| AZ State Indl. Dev. Auth. Ed. 144A Rev. Bonds, (BASIS Schools, Inc.), Ser. G, 5.00%, 7/1/37 | BB | 1500000 | 1503465 |
| Maricopa Cnty. Indl. Dev. Auth. 144A Rev. Bonds, (Commercial Metals Co), 4.00%, 10/15/47 | BB+ | 1550000 | 1315812 |
| Maricopa Cnty., Indl. Dev. Auth. Ed. Rev. Bonds, (Horizon Cmnty. Learning Ctr.), 5.00%, 7/1/35 | BB+ | 1500000 | 1494693 |
| Phoenix, Indl. Dev. Auth. Ed. Rev. Bonds, (Great Hearts Academies), 5.00%, 7/1/44 | BBB- | 3800000 | 3830766 |
| Phoenix, Indl. Dev. Auth. Ed. 144A Rev. Bonds, (BASIS Schools, Inc.) |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;Ser. A, 5.00%, 7/1/46 | BB | 750000 | 714191 |
| &nbsp;&nbsp;&nbsp;&nbsp;5.00%, 7/1/35 | BB | 1500000 | 1507815 |
| &nbsp;&nbsp;&nbsp;&nbsp;Ser. A, 5.00%, 7/1/35 | BB | 1750000 | 1759117 |
| Pima Cnty., Indl. Dev. Auth. Sr. Living 144A Rev. Bonds, (La Posada at Park Centre, Inc.) |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;7.00%, 11/15/57 | BBB+/P | 1650000 | 1716094 |
| &nbsp;&nbsp;&nbsp;&nbsp;6.875%, 11/15/52 | BBB+/P | 500000 | 520329 |
| &nbsp;&nbsp;&nbsp;&nbsp;6.75%, 11/15/42 | BBB+/P | 1000000 | 1046499 |
| &nbsp;&nbsp;&nbsp;&nbsp;6.25%, 11/15/35 | BBB+/P | 1060000 | 1103964 |

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<br>18 Tax-Free High Yield Fund

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---

| | | | |
|:---|:---|:---|:---|
| **MUNICIPAL BONDS AND NOTES (102.9%)\*** *cont.* | **Rating\*\*** | **Principal amount** | **Value** |
| **Arizona** *cont.* | **Arizona** *cont.* | **Arizona** *cont.* | **Arizona** *cont.* |
| Salt Verde, Fin. Corp. Gas Rev. Bonds |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;5.50%, 12/1/29 | A3 | $1525000 | $1681893 |
| &nbsp;&nbsp;&nbsp;&nbsp;5.00%, 12/1/32 | A3 | 1500000 | 1637534 |
| Yavapai Cnty., Indl. Dev. Ed. Auth. Rev. Bonds, (Agribusiness & Equine Ctr.), 5.00%, 3/1/32 | BB+ | 1470000 | 1470063 |
| Yavapai Cnty., Indl. Dev. Ed. Auth. 144A Rev. Bonds, Ser. A, 5.00%, 9/1/34 | BB+ | 500000 | 500077 |
|  |  |  | **24411780** |
| **California (12.4%)** | **California (12.4%)** | **California (12.4%)** | **California (12.4%)** |
| Bay Area Toll Auth. VRDN (San Francisco Bay Area), Ser. C, 0.87%, 4/1/53 | VMIG 1 | 3100000 | 3100000 |
| CA Cmnty. Hsg. Agcy. Essential Hsg. 144A Rev. Bonds |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;(Aster Apt.), Ser. A-1, 4.00%, 2/1/56 | BB+/P | 3275000 | 2892540 |
| &nbsp;&nbsp;&nbsp;&nbsp;(Fountains at Emerald Park), 4.00%, 8/1/46 | BB-/P | 4890000 | 4152346 |
| CA Hsg. Fin. Agcy. Muni. Certif. Rev. Bonds, Ser. 21-1, Class A, 3.50%, 11/20/35 | BBB+ | 2846419 | 2760001 |
| CA Muni. Fin. Auth. VRDN (Chevron USA, Inc.), 0.65%, 11/1/35 | VMIG 1 | 2500000 | 2500000 |
| CA Pub. Fin. Auth. VRDN, (Sharp Hlth. Care Oblig. Group), Ser. C, 0.45%, 8/1/52 | VMIG 1 | 1500000 | 1500000 |
| CA Pub. State Fin. Auth. Sr. Living 144A Rev. Bonds, (Enso Village Project), Ser. A |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;5.00%, 11/15/51 | B-/P | 1500000 | 1329058 |
| &nbsp;&nbsp;&nbsp;&nbsp;5.00%, 11/15/36 | B-/P | 750000 | 728127 |
| CA School Fin. Auth. Rev. Bonds, (2023 Union, LLC), Ser. A, 6.00%, 7/1/33 | BBB- | 1000000 | 1009462 |
| CA State Infrastructure & Econ. Dev. Bank 144A Rev. Bonds, (WFCS Holdings II, LLC), Ser. B, zero %, 1/1/61 | B-/P | 7435000 | 431501 |
| CA State Muni. Fin. Auth Mobile Home Park Rev. Bonds, (Caritas Affordable Hsg., Inc.), 5.25%, 8/15/39 | A- | 800000 | 817400 |
| CA State Poll. Control Fin. Auth. Rev. Bonds, (San Jose Wtr. Co.), 4.75%, 11/1/46 | A | 1700000 | 1740141 |
| CA State Tobacco Securitization Agcy. Rev. Bonds |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;Ser. B-2, zero %, 6/1/55 | BB/P | 20390000 | 3701743 |
| &nbsp;&nbsp;&nbsp;&nbsp;(Gold Country Settlement Funding Corp.), Ser. B-2, zero %, 6/1/55 | BB/P | 7850000 | 1748148 |
| CMFA Special Fin. Agcy. I 144A Rev. Bonds, (Social Bond), Ser. A-2, 4.00%, 4/1/56 | BB/P | 2500000 | 1998126 |
| CSCDA Cmnty. Impt. Auth. Rev. Bonds, (Pasadena Portfolio), Ser. A-2, 3.00%, 12/1/56 | BBB-/P | 4000000 | 2853544 |
| CSCDA Cmnty. Impt. Auth. 144A Rev. Bonds |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;(Pasadena Portfolio), 4.00%, 12/1/56 | BB/P | 2000000 | 1519104 |
| &nbsp;&nbsp;&nbsp;&nbsp;(Anaheim), 4.00%, 8/1/56 | BB/P | 4900000 | 4228190 |
| &nbsp;&nbsp;&nbsp;&nbsp;(Jefferson-Anaheim), 3.125%, 8/1/56 | BB+/P | 1900000 | 1410493 |
| &nbsp;&nbsp;&nbsp;&nbsp;(Essential Hsg.), Ser. A-2, 3.00%, 2/1/57 | BBB-/P | 5500000 | 3920645 |
| &nbsp;&nbsp;&nbsp;&nbsp;(Jefferson-Anaheim), 2.875%, 8/1/41 | BB+/P | 1570000 | 1372585 |
| Davis, Joint Unified School Dist. G.O. Bonds, (Yolo Cnty., Election 2018), BAM, 3.00%, 8/1/38 | AA | 3140000 | 2858652 |
| Golden State Tobacco Securitization Corp. Rev. Bonds, Ser. B-2, zero %, 6/1/66 | BB+/P | 32440000 | 4101684 |

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<br>Tax-Free High Yield Fund 19

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| | | | |
|:---|:---|:---|:---|
| **MUNICIPAL BONDS AND NOTES (102.9%)\*** *cont.* | **Rating\*\*** | **Principal amount** | **Value** |
| **California** *cont.* | **California** *cont.* | **California** *cont.* | **California** *cont.* |
| Hastings Campus HFA Rev. Bonds, (U. of CA Hastings College of the Law), Ser. A, 5.00%, 7/1/61 | BB-/P | $2500000 | $2062349 |
| Long Beach, Bond Fin. Auth. Rev. Bonds, (Natural Gas Purchase), Ser. A, 5.50%, 11/15/37 | A2 | 2000000 | 2276178 |
| Palm Desert, Special Tax, (Cmnty. Fac. Dist. 2021-1), 4.00%, 9/1/51 | B+/P | 650000 | 588949 |
| Sacramento, Special Tax, (Greenbriar Cmnty. Fac. Dist. No 2018-03) |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;4.00%, 9/1/50 | BB/P | 600000 | 512461 |
| &nbsp;&nbsp;&nbsp;&nbsp;4.00%, 9/1/46 | BB/P | 750000 | 654467 |
| San Francisco, City & Cnty. Arpt. Comm. Intl. Arpt. VRDN, Ser. B, 1.05%, 5/1/58 | VMIG 1 | 13005000 | 13005000 |
| San Francisco, City & Cnty. Redev. Agcy. Cmnty. Successor Special Tax Bonds, (No. 6 Mission Bay Pub. Impts.), Ser. C, zero %, 8/1/43 | BBB/P | 8000000 | 2421913 |
| Santa Clara Cnty., Fin. Auth. Rev. Bonds, Ser. Q, 3.00%, 5/15/34 | AA+ | 6715000 | 6720143 |
| Sunnyvale, Special Tax Bonds, (Cmnty. Fac. Dist. No. 1), 7.75%, 8/1/32 | B+/P | 3550000 | 3563287 |
| Tobacco Securitization Auth. of Southern CA Rev. Bonds, Ser. B-2, Class 2, zero %, 6/1/54 | BB/P | 14660000 | 2707500 |
|  |  |  | **87185737** |
| **Colorado (4.5%)** | **Colorado (4.5%)** | **Colorado (4.5%)** | **Colorado (4.5%)** |
| CO Pub. Hwy. Auth. Rev. Bonds, (E-470), zero %, 9/1/41 | A2 | 1000000 | 462159 |
| CO State Hlth. Fac. Auth. Hosp. Rev. Bonds |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;(Frasier Meadows Retirement Cmnty.), Ser. A, 5.25%, 5/15/47 | BBB-/F | 250000 | 237802 |
| &nbsp;&nbsp;&nbsp;&nbsp;(Frasier Meadows Retirement Cmnty.), Ser. A, 5.25%, 5/15/37 | BBB-/F | 1000000 | 991986 |
| &nbsp;&nbsp;&nbsp;&nbsp;(Frasier Meadows Retirement Cmnty.), Ser. B, 5.00%, 5/15/39 (Prerefunded 5/15/23) | BBB-/F | 2000000 | 2013406 |
| &nbsp;&nbsp;&nbsp;&nbsp;(Christian Living Neighborhood), 5.00%, 1/1/31 | BB/P | 2000000 | 1940173 |
| &nbsp;&nbsp;&nbsp;&nbsp;(Covenant Living Cmnty. and Svcs. Oblig. Group), 4.00%, 12/1/50 | A-/F | 1700000 | 1450884 |
| &nbsp;&nbsp;&nbsp;&nbsp;(Christian Living Neighborhoods Oblig. Group), 4.00%, 1/1/42 | BB/P | 1000000 | 764320 |
| &nbsp;&nbsp;&nbsp;&nbsp;(Covenant Living Cmnty. and Svcs. Oblig. Group), 4.00%, 12/1/40 | A-/F | 2000000 | 1810348 |
| &nbsp;&nbsp;&nbsp;&nbsp;(Christian Living Neighborhoods), 4.00%, 1/1/38 | BBB/P | 550000 | 442560 |
| Denver City & Cnty., Arpt. Rev. Bonds |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;Ser. D, 5.75%, 11/15/37 <sup>T</sup> | Aa3 | 2500000 | 2982388 |
| &nbsp;&nbsp;&nbsp;&nbsp;Ser. D, 5.75%, 11/15/38 <sup>T</sup> | Aa3 | 3175000 | 3783830 |
| Plaza, Tax Alloc. Bonds, (Metro. Dist. No. 1), 5.00%, 12/1/40 | BB-/P | 3000000 | 2964930 |
| Pub. Auth. for CO Energy Rev. Bonds, (Natural Gas Purchase), 6.50%, 11/15/38 | A2 | 2000000 | 2480329 |
| RainDance Metro. Dist. No. 1 Rev. Bonds, (Non-Potable Wtr. Enterprise) |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;5.25%, 12/1/50 | B+/P | 1375000 | 1267865 |
| &nbsp;&nbsp;&nbsp;&nbsp;5.00%, 12/1/40 | B+/P | 625000 | 592449 |

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<br>20 Tax-Free High Yield Fund

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---

| | | | |
|:---|:---|:---|:---|
| **MUNICIPAL BONDS AND NOTES (102.9%)\*** *cont.* | **Rating\*\*** | **Principal amount** | **Value** |
| **Colorado** *cont.* | **Colorado** *cont.* | **Colorado** *cont.* | **Colorado** *cont.* |
| Rampart Range Metro. Distr. Rev. Bonds, (Dist. No. 5), 4.00%, 12/1/51 | BB-/P | $2000000 | $1431113 |
| Southlands, Metro. Dist. No. 1 G.O. Bonds, Ser. A-1, 5.00%, 12/1/37 | Ba1 | 500000 | 500433 |
| Trails at Crowfoot Metro. Dist. No. 3 G.O. Bonds, Ser. A, 5.00%, 12/1/49 | B+/P | 2000000 | 1855154 |
| Village Metro. Dist. G.O. Bonds |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;5.00%, 12/1/49 | BB/P | 1250000 | 1193100 |
| &nbsp;&nbsp;&nbsp;&nbsp;5.00%, 12/1/40 | BB/P | 1000000 | 977434 |
| Windler Pub. Impt. Auth. Rev. Bonds, Ser. A-1, 4.125%, 12/1/51 | B+/P | 2000000 | 1419780 |
|  |  |  | **31562443** |
| **Connecticut (1.1%)** | **Connecticut (1.1%)** | **Connecticut (1.1%)** | **Connecticut (1.1%)** |
| CT State Hlth. & Edl. Fac. Auth. Rev. Bonds |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;(Masonicare Issue), Ser. F, 5.00%, 7/1/33 | BBB+/F | 1500000 | 1505066 |
| &nbsp;&nbsp;&nbsp;&nbsp;(Stamford Hosp. Oblig. Group (The)), Ser. M, 4.00%, 7/1/42 | BBB+ | 2000000 | 1867896 |
| &nbsp;&nbsp;&nbsp;&nbsp;(Stamford Hosp. Oblig. Group (The)), Ser. M, 4.00%, 7/1/38 | BBB+ | 865000 | 842004 |
| CT State Hlth. & Edl. Fac. Auth. 144A Rev. Bonds, (Church Home of Hartford, Inc.), Ser. A, 5.00%, 9/1/46 | BB/F | 1000000 | 926871 |
| Harbor Point Infrastructure Impt. Dist. 144A Tax Alloc. Bonds, (Harbor Point Ltd.), 5.00%, 4/1/39 | BB/P | 2500000 | 2502900 |
|  |  |  | **7644737** |
| **Delaware (0.9%)** | **Delaware (0.9%)** | **Delaware (0.9%)** | **Delaware (0.9%)** |
| DE State Econ. Dev. Auth. Rev. Bonds, (ASPIRA Charter School), Ser. A |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;5.00%, 6/1/46 | BB | 1820000 | 1783047 |
| &nbsp;&nbsp;&nbsp;&nbsp;5.00%, 6/1/36 | BB | 700000 | 706145 |
| Millsboro Special Oblig. 144A Special Tax, (Plantation Lakes), 5.25%, 7/1/48 | BB-/P | 1999000 | 1965966 |
| Millsboro Special Oblig. 144A Tax Alloc. Bonds, (Plantation Lakes Special Dev. Dist.), 5.125%, 7/1/38 | BB-/P | 1498000 | 1499194 |
|  |  |  | **5954352** |
| **District of Columbia (2.7%)** | **District of Columbia (2.7%)** | **District of Columbia (2.7%)** | **District of Columbia (2.7%)** |
| DC Rev. Bonds |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;(Plenary Infrastructure DC, LLC), 5.50%, 8/31/34 | A3 | 3755000 | 4252927 |
| &nbsp;&nbsp;&nbsp;&nbsp;(Ingleside at Rock Creek), Ser. A, 5.00%, 7/1/52 | BB-/P | 3170000 | 2711122 |
| &nbsp;&nbsp;&nbsp;&nbsp;(Latin American Montessori Bilingual Pub. Charter School Oblig. Group), 5.00%, 6/1/40 | BB+ | 2750000 | 2727782 |
| &nbsp;&nbsp;&nbsp;&nbsp;(Kipp DC), Ser. B, 5.00%, 7/1/37 | BBB+ | 3315000 | 3418233 |
| &nbsp;&nbsp;&nbsp;&nbsp;(KIPP DC), 4.00%, 7/1/49 | BBB+ | 1000000 | 855114 |
| &nbsp;&nbsp;&nbsp;&nbsp;(KIPP DC), 4.00%, 7/1/44 | BBB+ | 250000 | 221566 |
| DC 144A Rev. Bonds, (Rocketship DC Oblig. Group), Ser. 21-A, 5.00%, 6/1/61 | BB/P | 700000 | 647402 |
| Metro. Washington, Arpt. Auth. Dulles Toll Rd. Rev. Bonds, Cap Apprec 2nd Sr Lien, Ser. B, zero %, 10/1/40 | A- | 995000 | 465518 |

---

<br>Tax-Free High Yield Fund 21

------

---

| | | | |
|:---|:---|:---|:---|
| **MUNICIPAL BONDS AND NOTES (102.9%)\*** *cont.* | **Rating\*\*** | **Principal amount** | **Value** |
| **District of Columbia** *cont.* | **District of Columbia** *cont.* | **District of Columbia** *cont.* | **District of Columbia** *cont.* |
| Metro. Washington DC, Arpt. Auth. Dulles Toll Rd. Rev. Bonds |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;(Dulles Metrorail & Cap. Impt. Proj.) Ser. B, 4.00%, 10/1/44 <sup>T</sup> | A- | $1940000 | $1895811 |
| &nbsp;&nbsp;&nbsp;&nbsp;(Dulles Metrorail & Cap. Impt. Proj.) 4.00%, 10/1/53 <sup>T</sup> | A- | 1935000 | 1814807 |
|  |  |  | **19010282** |
| **Florida (6.8%)** | **Florida (6.8%)** | **Florida (6.8%)** | **Florida (6.8%)** |
| Cap. Projects Fin. Auth. Rev. Bonds, (CAPFA Cap. Corp. 2000F), Ser. A-1, 5.00%, 10/1/33 | Baa3 | 2000000 | 2052354 |
| Cap. Trust Agcy. Rev. Bonds, (Wonderful Foundation Charter School Holdings, LLC), zero %, 1/1/60 | B/P | 6000000 | 363682 |
| Cap. Trust Agcy. 144A Rev. Bonds, (Wonderful Foundation Charter School Holdings, LLC), 5.00%, 1/1/55 | BB-/P | 3800000 | 3164538 |
| Cap. Trust Agcy. Edl. Fac. Rev. Bonds, (Liza Jackson Preparatory School, Inc.) |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;5.00%, 8/1/55 | Baa3 | 1000000 | 1011882 |
| &nbsp;&nbsp;&nbsp;&nbsp;5.00%, 8/1/40 | Baa3 | 300000 | 309903 |
| Fishhawk, CCD IV Special Assmt. Bonds, 7.25%, 5/1/43 | B/P | 540000 | 543522 |
| FL State Dev. Fin. Corp. Ed. Fac. 144A Rev. Bonds, (Drs. Kiran & Pallavi Patel 2017 Foundation for Global Understanding, Inc.), 4.00%, 7/1/51 | BB/P | 1000000 | 795297 |
| FL State Higher Edl. Fac. Financial Auth. Rev. Bonds |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;(St. Leo U., Inc. Oblig. Group), 5.00%, 3/1/49 | BB+ | 3930000 | 3558617 |
| &nbsp;&nbsp;&nbsp;&nbsp;(St. Leo U.), 5.00%, 3/1/44 | BB+ | 3500000 | 3237815 |
| Lake Cnty., Retirement Fac. Rev. Bonds, (Waterman Cmnty., Inc.), 5.75%, 8/15/55 | B/P | 1750000 | 1543387 |
| Lakewood Ranch, Stewardship Dist. Special Assessment Bonds, (Village of Lakewood Ranch South), 5.00%, 5/1/36 | B+/P | 815000 | 822153 |
| Lakewood Ranch, Stewardship Dist. 144A Special Assmt., 4.00%, 5/1/50 | B/P | 500000 | 402072 |
| Lakewood Ranch, Stewardship Dist. 144A Special Assmt. Bonds, (Northeast Sector), 5.30%, 5/1/39 | B-/P | 1250000 | 1271844 |
| Lee Cnty., Indl. Dev. Auth. Rev. Bonds, (Shell Point/Waterside Hlth.), 5.00%, 11/15/39 | BBB+ | 750000 | 759847 |
| Miami-Dade Cnty., Indl. Dev. Auth. Rev. Bonds, (Pinecrest Academy, Inc.), 5.00%, 9/15/34 | BBB | 2195000 | 2251577 |
| Middleton, Cmnty. Dev. Dist. 144A Special Assmt. Bonds, (Dist. A), 6.20%, 5/1/53 | B+/P | 1355000 | 1395102 |
| Orange Cnty., Hlth. Fac. Auth. Rev. Bonds, (Orlando Hlth.), 5.00%, 10/1/53 | A+ | 7735000 | 8322264 |
| Palm Beach Cnty., Rev. Bonds, (Lynn U. Hsg.), Ser. A, 5.00%, 6/1/57 | B+/P | 1045000 | 932355 |
| Palm Beach Cnty., 144A Rev. Bonds, (PBAU Hsg.), Ser. A, 5.00%, 4/1/39 | Ba1 | 500000 | 488587 |
| Pinellas Cnty., Indl. Dev. Auth. Rev. Bonds, (2017 Foundation for Global Understanding, Inc.), 5.00%, 7/1/39 | AAA/P | 2770000 | 2768617 |

---

<br>22 Tax-Free High Yield Fund

------

---

| | | | |
|:---|:---|:---|:---|
| **MUNICIPAL BONDS AND NOTES (102.9%)\*** *cont.* | **Rating\*\*** | **Principal amount** | **Value** |
| **Florida** *cont.* | **Florida** *cont.* | **Florida** *cont.* | **Florida** *cont.* |
| Sarasota Cnty., Hlth. Fac. Auth. Retirement Fac. Rev. Bonds, (Village of Isle) |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;5.00%, 1/1/31 | BB+/F | $1285000 | $1257039 |
| &nbsp;&nbsp;&nbsp;&nbsp;5.00%, 1/1/30 | BB+/F | 750000 | 737507 |
| Southeast Overtown Park West Cmnty. Redev. Agcy. 144A Tax Alloc. Bonds, Ser. A-1, 5.00%, 3/1/30 | BBB+ | 1440000 | 1468666 |
| St. John's Cnty., Indl. Dev. Auth. Rev. Bonds, (Life Care Ponte Vedra Oblig. Group), Ser. A |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;4.00%, 12/15/50 | BB+/F | 750000 | 559503 |
| &nbsp;&nbsp;&nbsp;&nbsp;4.00%, 12/15/41 | BB+/F | 750000 | 606725 |
| &nbsp;&nbsp;&nbsp;&nbsp;4.00%, 12/15/36 | BB+/F | 400000 | 346511 |
| Tampa, Cap. Impt. Cigarette Tax Rev. Bonds, (Cap. Appn.), Ser. A |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;zero %, 9/1/53 | A1 | 2600000 | 589986 |
| &nbsp;&nbsp;&nbsp;&nbsp;zero %, 9/1/45 | A1 | 2000000 | 693074 |
| &nbsp;&nbsp;&nbsp;&nbsp;zero %, 9/1/41 | A1 | 1000000 | 446459 |
| &nbsp;&nbsp;&nbsp;&nbsp;zero %, 9/1/40 | A1 | 850000 | 404639 |
| Village Cmnty. Dev. Dist. No. 10 Special Assmt. Bonds, 5.75%, 5/1/31 | BB/P | 925000 | 928410 |
| Village, Special Assmt., (Cmnty. Dev. Dist. No. 13), 3.25%, 5/1/52 | BB-/P | 1500000 | 1048817 |
| Village, 144A Special Assmt., (Village Cmnty. Dev. Dist. No. 13), 3.50%, 5/1/51 | BB-/P | 3885000 | 2880157 |
|  |  |  | **47962908** |
| **Georgia (1.5%)** | **Georgia (1.5%)** | **Georgia (1.5%)** | **Georgia (1.5%)** |
| Cobb Cnty., Dev. Auth. Student Hsg. Rev. Bonds |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;(Kennesaw State U. Real Estate Oblig. Group), Ser. C, 5.00%, 7/15/38 | Baa2 | 1250000 | 1260001 |
| &nbsp;&nbsp;&nbsp;&nbsp;(Kennesaw State U. Real Estate), 5.00%, 7/15/30 | Baa2 | 1200000 | 1222688 |
| Geo L Smith II GA Congress Ctr. 144A Rev. Bonds, (Signia Hotel Mgt., LLC.) |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;5.00%, 1/1/54 | BB-/P | 2470000 | 2038166 |
| &nbsp;&nbsp;&nbsp;&nbsp;5.00%, 1/1/36 | BB-/P | 1430000 | 1338149 |
| Muni. Election Auth. of GA Rev. Bonds, (Plant Vogtle Units 3 & 4) |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;4.50%, 7/1/63 | A | 1500000 | 1506888 |
| &nbsp;&nbsp;&nbsp;&nbsp;Ser. A, 4.00%, 1/1/59 | A2 | 3000000 | 2805177 |
|  |  |  | **10171069** |
| **Illinois (8.6%)** | **Illinois (8.6%)** | **Illinois (8.6%)** | **Illinois (8.6%)** |
| Chicago, G.O. Bonds |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;Ser. A, 5.50%, 1/1/49 | BBB+ | 2000000 | 2080980 |
| &nbsp;&nbsp;&nbsp;&nbsp;Ser. A, 5.00%, 1/1/44 | BBB+ | 2000000 | 2009554 |
| &nbsp;&nbsp;&nbsp;&nbsp;Ser. A, 5.00%, 1/1/31 | BBB+ | 1400000 | 1501585 |
| &nbsp;&nbsp;&nbsp;&nbsp;Ser. A, 5.00%, 1/1/30 | BBB+ | 2600000 | 2793970 |
| &nbsp;&nbsp;&nbsp;&nbsp;Ser. B, 4.00%, 1/1/38 | BBB+ | 7553000 | 7103186 |
| &nbsp;&nbsp;&nbsp;&nbsp;Ser. A, 4.00%, 1/1/36 | BBB+ | 3150000 | 3062831 |
| Chicago, Special Assmt. |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;3.45%, 12/1/32 | BBB/P | 300000 | 267101 |
| &nbsp;&nbsp;&nbsp;&nbsp;3.29%, 12/1/30 | BBB/P | 350000 | 315471 |
| &nbsp;&nbsp;&nbsp;&nbsp;3.20%, 12/1/29 | BBB/P | 325000 | 294668 |
| &nbsp;&nbsp;&nbsp;&nbsp;2.87%, 12/1/27 | BBB/P | 255000 | 236319 |

---

<br>Tax-Free High Yield Fund 23

------

---

| | | | |
|:---|:---|:---|:---|
| **MUNICIPAL BONDS AND NOTES (102.9%)\*** *cont.* | **Rating\*\*** | **Principal amount** | **Value** |
| **Illinois** *cont.* | **Illinois** *cont.* | **Illinois** *cont.* | **Illinois** *cont.* |
| Chicago, Board of Ed. G.O. Bonds, Ser. H, 5.00%, 12/1/36 | BB | $4600000 | $4695859 |
| Chicago, Board of Ed. 144A G.O. Bonds, Ser. A, 7.00%, 12/1/46 | BB | 1500000 | 1645963 |
| Chicago, O'Hare Intl. Arpt. Rev. Bonds, Ser. A, AGM, 5.50%, 1/1/53 | AA | 3800000 | 4124402 |
| Du Page Cnty., Special Svc. Area No. 31 Special Tax Bonds, (Monarch Landing), 5.625%, 3/1/36 | B/P | 698000 | 696647 |
| IL State G.O. Bonds |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;Ser. A, 5.25%, 12/1/30 | Baa1 | 5000000 | 5382026 |
| &nbsp;&nbsp;&nbsp;&nbsp;Ser. A, 5.00%, 10/1/33 | Baa1 | 1025000 | 1092592 |
| &nbsp;&nbsp;&nbsp;&nbsp;Ser. A, 5.00%, 12/1/31 | Baa1 | 7200000 | 7648344 |
| &nbsp;&nbsp;&nbsp;&nbsp;Ser. C, 5.00%, 11/1/29 | Baa1 | 2000000 | 2136894 |
| IL State Fin. Auth. Rev. Bonds |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;(Plymouth Place), 5.25%, 5/15/50 (Prerefunded 5/15/25) | AAA/P | 850000 | 904811 |
| &nbsp;&nbsp;&nbsp;&nbsp;(Rosalind Franklin U. of Medicine & Science), Ser. A, 5.00%, 8/1/47 | BBB+ | 850000 | 857967 |
| &nbsp;&nbsp;&nbsp;&nbsp;(Rosalind Franklin U. of Medicine & Science), Ser. A, 5.00%, 8/1/42 | BBB+ | 500000 | 507146 |
| &nbsp;&nbsp;&nbsp;&nbsp;(Rosalind Franklin U. of Medicine and Science), Ser. A, 5.00%, 8/1/34 | BBB+ | 650000 | 677810 |
| &nbsp;&nbsp;&nbsp;&nbsp;(Southern IL Healthcare Enterprises, Inc.), 5.00%, 3/1/33 | A | 200000 | 213500 |
| IL State Fin. Auth. Student Hsg. & Academic Fac. Rev. Bonds, (CHF-Chicago, LLC), 5.00%, 2/15/47 | Baa3 | 5500000 | 5510938 |
| Metro. Pier & Exposition Auth. Rev. Bonds, (McCormick Place Expansion), Ser. B, stepped-coupon zero % (4.850%, 6/15/31), 12/15/42 <sup>††</sup> | A- | 3000000 | 1867133 |
| Northern IL U. Rev. Bonds, Ser. B, BAM |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;5.00%, 4/1/34 | AA | 650000 | 713559 |
| &nbsp;&nbsp;&nbsp;&nbsp;5.00%, 4/1/29 | AA | 400000 | 441551 |
| &nbsp;&nbsp;&nbsp;&nbsp;4.00%, 4/1/41 | AA | 625000 | 604757 |
| &nbsp;&nbsp;&nbsp;&nbsp;4.00%, 4/1/38 | AA | 600000 | 599543 |
| &nbsp;&nbsp;&nbsp;&nbsp;4.00%, 4/1/37 | AA | 600000 | 602439 |
|  |  |  | **60589546** |
| **Kansas (0.3%)** | **Kansas (0.3%)** | **Kansas (0.3%)** | **Kansas (0.3%)** |
| Wichita, Hlth. Care Fac. Rev. Bonds, (Presbyterian Manors), Ser. I, 5.00%, 5/15/38 | BB-/P | 1000000 | 920491 |
| Wyandotte, Cnty./Kansas City, Unified Govt. 144A Rev. Bonds, (Legends Apt. Garage & West Lawn), 4.50%, 6/1/40 | BB+/P | 1175000 | 1084255 |
|  |  |  | **2004746** |
| **Kentucky (0.5%)** | **Kentucky (0.5%)** | **Kentucky (0.5%)** | **Kentucky (0.5%)** |
| KY Econ. Dev. Fin. Auth. Rev. Bonds, (Masonic Home Indpt. Living), 5.00%, 5/15/36 | BB/P | 2000000 | 1765558 |
| KY State Econ. Dev. Fin. Auth. Rev. Bonds, (Owensboro Hlth.), Ser. A, 5.25%, 6/1/41 | Baa2 | 375000 | 387906 |
| KY State Econ. Dev. Fin. Auth. Hlth. Care Rev. Bonds, (Masonic Homes of KY), 5.375%, 11/15/42 | BB-/P | 1400000 | 1214683 |
|  |  |  | **3368147** |

---

<br>24 Tax-Free High Yield Fund

------

---

| | | | |
|:---|:---|:---|:---|
| **MUNICIPAL BONDS AND NOTES (102.9%)\*** *cont.* | **Rating\*\*** | **Principal amount** | **Value** |
| **Louisiana (0.1%)** | **Louisiana (0.1%)** | **Louisiana (0.1%)** | **Louisiana (0.1%)** |
| St. Tammany, Public Trust Fin. Auth. Rev. Bonds, (Christwood), 5.25%, 11/15/37 | BB/P | $765000 | $750298 |
|  |  |  | **750298** |
| **Maine (0.1%)** | **Maine (0.1%)** | **Maine (0.1%)** | **Maine (0.1%)** |
| ME State Fin. Auth. Solid Waste Disp. 144A Mandatory Put Bonds (8/1/25), (Casella Waste Syst.), 5.125%, 8/1/35 | B1 | 1000000 | 1008263 |
|  |  |  | **1008263** |
| **Maryland (2.0%)** | **Maryland (2.0%)** | **Maryland (2.0%)** | **Maryland (2.0%)** |
| Brunswick, Special Tax, 5.00%, 7/1/36 | B+/P | 999000 | 1019998 |
| Frederick Cnty., Edl. Fac. 144A Rev. Bonds, (Mount St. Mary's U.), Ser. A, 5.00%, 9/1/37 | BB+ | 500000 | 486856 |
| MD Econ. Dev. Corp. Rev. Bonds, (Morgan View & Thurgood Marshall Student Hsg.), Ser. A, 6.00%, 7/1/58 | BBB- | 5025000 | 5589873 |
| MD State Econ. Dev. Corp. Tax Alloc. Bonds, (Port Covington), 4.00%, 9/1/50 | B+/P | 1250000 | 1049197 |
| Prince Georges Cnty., Special Oblig. 144A Tax Alloc. Bonds, (Westphalia Town Ctr.) |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;5.25%, 7/1/48 | B/P | 2000000 | 2003916 |
| &nbsp;&nbsp;&nbsp;&nbsp;5.125%, 7/1/39 | B/P | 300000 | 300759 |
| Westminster, Rev. Bonds |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;(Lutheran Village at Miller's Grant, Inc. (The)), Ser. A, 6.00%, 7/1/34 | B-/P | 750000 | 760077 |
| &nbsp;&nbsp;&nbsp;&nbsp;(Carroll Lutheran Village, Inc.), 5.125%, 7/1/34 (Prerefunded 7/1/24) | BB/P | 3000000 | 3108035 |
|  |  |  | **14318711** |
| **Massachusetts (2.3%)** | **Massachusetts (2.3%)** | **Massachusetts (2.3%)** | **Massachusetts (2.3%)** |
| Lowell, Collegiate Charter School Rev. Bonds, 5.00%, 6/15/49 | BB-/P | 2290000 | 2192864 |
| MA State Dev. Fin. Agcy. Rev. Bonds |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;(Loomis Communities), Ser. A, U.S. Govt. Coll., 6.00%, 1/1/33 (Prerefunded 3/6/23) | AAA/P | 250000 | 253648 |
| &nbsp;&nbsp;&nbsp;&nbsp;(Milford Regl. Med. Ctr. Oblig. Group), Ser. F, 5.75%, 7/15/43 | B+ | 1000000 | 1002800 |
| MA State Dev. Fin. Agcy. VRDN, (Boston U.), Ser. U-6E, 1.15%, 10/1/42 | VMIG 1 | 3185000 | 3185000 |
| MA State Dev. Fin. Agcy. 144A Rev. Bonds, (Linden Ponds, Inc. Fac.), 5.125%, 11/15/46 | A/F | 2000000 | 2067206 |
| MA State Dev. Fin. Agcy. VRDN (Boston U.), Ser. U-6C, 1.15%, 10/1/42 | VMIG 1 | 3500000 | 3500000 |
| MA State Dev. Fin. Agcy. Hlth. Care Fac. 144A Rev. Bonds, (Adventcare), Ser. A, 6.65%, 10/15/28 (In default) <sup>†</sup> | D/P | 2035000 | 203500 |
| MA State Hlth. & Edl. Fac. Auth. VRDN (MA Inst. of Tech.), 1.45%, 7/1/31 | VMIG 1 | 500000 | 500000 |
| MA State Trans. Fund Rev. Bonds, (Rail Enhancement Program), Ser. A, 5.00%, 6/1/50 | Aa1 | 3200000 | 3546996 |
|  |  |  | **16452014** |

---

<br>Tax-Free High Yield Fund 25

------

---

| | | | |
|:---|:---|:---|:---|
| **MUNICIPAL BONDS AND NOTES (102.9%)\*** *cont.* | **Rating\*\*** | **Principal amount** | **Value** |
| **Michigan (1.6%)** | **Michigan (1.6%)** | **Michigan (1.6%)** | **Michigan (1.6%)** |
| Detroit, G.O. Bonds |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;5.00%, 4/1/37 | Ba2 | $350000 | $357580 |
| &nbsp;&nbsp;&nbsp;&nbsp;5.00%, 4/1/36 | Ba2 | 1400000 | 1438443 |
| Flint, Hosp. Bldg. Auth. Rev. Bonds, Ser. A, 5.25%, 7/1/39 | Ba1 | 500000 | 501486 |
| MI State Fin. Auth. Ltd. Oblig. Rev. Bonds, (Lawrence Technological U.) |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;5.25%, 2/1/32 | BBB- | 1000000 | 1033595 |
| &nbsp;&nbsp;&nbsp;&nbsp;5.00%, 2/1/47 | BBB- | 4100000 | 3925507 |
| &nbsp;&nbsp;&nbsp;&nbsp;5.00%, 2/1/37 | BBB- | 1080000 | 1086870 |
| MI State Fin. Auth. Ltd. Oblig. Higher Ed. Fac. Rev. Bonds, (Aquinas College), 5.00%, 5/1/46 | BB/P | 2000000 | 1741790 |
| MI State Strategic Fund Ltd. Oblig. Rev. Bonds, (Holland Home Oblig. Group) |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;5.00%, 11/15/43 | BBB-/F | 500000 | 498042 |
| &nbsp;&nbsp;&nbsp;&nbsp;5.00%, 11/15/34 | BBB-/F | 1000000 | 1016027 |
|  |  |  | **11599340** |
| **Minnesota (1.4%)** | **Minnesota (1.4%)** | **Minnesota (1.4%)** | **Minnesota (1.4%)** |
| Baytown Twp., Lease Rev. Bonds, Ser. A, 4.00%, 8/1/36 | BB+ | 400000 | 348953 |
| Duluth, COP, (Indpt. School Dist. No. 709), Ser. A |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;4.20%, 3/1/34 | Baa3 | 725000 | 695760 |
| &nbsp;&nbsp;&nbsp;&nbsp;4.00%, 3/1/28 | Baa3 | 760000 | 749330 |
| &nbsp;&nbsp;&nbsp;&nbsp;4.00%, 3/1/27 | Baa3 | 730000 | 724826 |
| Forest Lake, Charter School Lease Rev. Bonds, (LILA Bldg. Co.), Ser. A, 5.25%, 8/1/43 | BB+ | 615000 | 615334 |
| Ham Lake, Charter School Lease Rev. Bonds |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;(DaVinci Academy of Arts & Science), Ser. A, 5.00%, 7/1/47 | BB-/P | 1000000 | 933216 |
| &nbsp;&nbsp;&nbsp;&nbsp;(Parnassus Preparatory School), Ser. A, 5.00%, 11/1/36 | BB+ | 1500000 | 1488113 |
| MN State Higher Ed. Fac. Auth. Rev. Bonds, (Augsburg U.), Ser. A, 5.00%, 5/1/46 | Ba1 | 1000000 | 944778 |
| Rochester, Hlth. Care Fac. VRDN, (Mayo Clinic), Ser. B, 1.90%, 11/15/38 | VMIG 1 | 800000 | 800000 |
| St. Paul, Hsg. & Redev. Auth. Charter School Lease Rev. Bonds, (Hmong College Preparatory Academy), 5.00%, 9/1/55 | BB+ | 2750000 | 2531733 |
|  |  |  | **9832043** |
| **Missouri (1.7%)** | **Missouri (1.7%)** | **Missouri (1.7%)** | **Missouri (1.7%)** |
| Kansas City, Indl. Dev. Auth. Arpt. Special Oblig. Rev. Bonds |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;5.00%, 3/1/46 | A2 | 3060000 | 3183674 |
| &nbsp;&nbsp;&nbsp;&nbsp;AGM, 4.00%, 3/1/57 | AA | 1300000 | 1221842 |
| Plaza at Noah's Ark Cmnty. Impt. Dist. Rev. Bonds |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;3.125%, 5/1/35 | B+/P | 500000 | 424792 |
| &nbsp;&nbsp;&nbsp;&nbsp;3.00%, 5/1/30 | B+/P | 725000 | 662017 |
| Saint Louis, Indl. Dev. Auth. Fin. Rev. Bonds, (Ballpark Village Dev.), Ser. A, 4.75%, 11/15/47 | BB-/P | 1625000 | 1248618 |

---

<br>26 Tax-Free High Yield Fund

------

---

| | | | |
|:---|:---|:---|:---|
| **MUNICIPAL BONDS AND NOTES (102.9%)\*** *cont.* | **Rating\*\*** | **Principal amount** | **Value** |
| **Missouri** *cont.* | **Missouri** *cont.* | **Missouri** *cont.* | **Missouri** *cont.* |
| St. Louis Cnty., Indl. Dev. Auth. Sr. Living Fac. Rev. Bonds, (Friendship Village) |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;5.25%, 9/1/53 | BB+/F | $4250000 | $3939760 |
| &nbsp;&nbsp;&nbsp;&nbsp;5.00%, 9/1/48 | BB+/F | 1750000 | 1590410 |
|  |  |  | **12271113** |
| **Montana (1.8%)** | **Montana (1.8%)** | **Montana (1.8%)** | **Montana (1.8%)** |
| MT State Board of Regents Higher Ed. Mandatory Put Bonds (11/15/22), U. of MT, AGM, 5.25%, 11/15/52 <sup>T</sup> | AA | 6665000 | 7494001 |
| MT State Fac. Fin. Auth. Rev. Bonds, (Billings Clinic Oblig. Group), Ser. A |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;5.00%, 8/15/33 | AA- | 1100000 | 1308642 |
| &nbsp;&nbsp;&nbsp;&nbsp;5.00%, 8/15/30 | AA- | 1275000 | 1486809 |
| &nbsp;&nbsp;&nbsp;&nbsp;4.00%, 8/15/37 | AA- | 1250000 | 1296449 |
| &nbsp;&nbsp;&nbsp;&nbsp;4.00%, 8/15/36 | AA- | 1250000 | 1306283 |
|  |  |  | **12892184** |
| **Nevada (0.7%)** | **Nevada (0.7%)** | **Nevada (0.7%)** | **Nevada (0.7%)** |
| Clark Cnty., Impt. Dist. No. 159 Special Assessment Bonds, (Summerlin Village 16A), 5.00%, 8/1/35 | B+/P | 590000 | 597695 |
| Las Vegas, Special Assmt. Bonds |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;5.00%, 6/1/30 | B+/P | 915000 | 923143 |
| &nbsp;&nbsp;&nbsp;&nbsp;(Special Impt. Dist. No. 816), 3.125%, 6/1/46 | BB-/P | 1300000 | 904638 |
| Las Vegas, Impt. Dist. No. 812 Special Assessment Bonds, (Summerlin Village 24), 5.00%, 12/1/35 | B/P | 685000 | 692793 |
| North Las Vegas, Local Impt. Special Assmt. Bonds, (Valley Vista Special Impt. Dist. No. 64), 4.50%, 6/1/39 | B/P | 675000 | 652562 |
| NV State Dept. of Bus. & Indl. 144A Rev. Bonds, (Somerset Academy), Ser. A, 5.00%, 12/15/48 | BB | 1000000 | 964780 |
|  |  |  | **4735611** |
| **New Hampshire (0.9%)** | **New Hampshire (0.9%)** | **New Hampshire (0.9%)** | **New Hampshire (0.9%)** |
| National Fin. Auth. Rev. Bonds, (Caritas Acquisitions VII, LLC), Ser. A |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;4.50%, 8/15/55 | BBB/P | 3495000 | 2996345 |
| &nbsp;&nbsp;&nbsp;&nbsp;4.25%, 8/15/46 | BBB/P | 1650000 | 1410602 |
| &nbsp;&nbsp;&nbsp;&nbsp;4.125%, 8/15/40 | BBB/P | 1475000 | 1293992 |
| NH State Hlth. & Ed. Fac. Auth. Rev. Bonds, (Kendel at Hanover), 5.00%, 10/1/46 | BBB+/F | 625000 | 627774 |
| NH State Hlth. & Ed. Fac. Auth. 144A Rev. Bonds, (Hillside Village), Ser. A |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;6.25%, 7/1/42 (In default) <sup>†</sup> | D/P | 208697 | 45913 |
| &nbsp;&nbsp;&nbsp;&nbsp;6.125%, 7/1/37 (In default) <sup>†</sup> | D/P | 834787 | 183653 |
|  |  |  | **6558279** |
| **New Jersey (4.4%)** | **New Jersey (4.4%)** | **New Jersey (4.4%)** | **New Jersey (4.4%)** |
| Camden Cnty., Impt. Auth. School Rev. Bonds, (KIPP Cooper Norcross), 6.00%, 6/15/62 | BBB | 3000000 | 3179123 |
| NJ State Econ. Dev. Auth. Rev. Bonds |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;(Paterson Charter School Science & Tech.), Ser. A, 6.10%, 7/1/44 | BB | 655000 | 655581 |
| &nbsp;&nbsp;&nbsp;&nbsp;(Paterson Charter School Science & Tech.), Ser. A, 6.00%, 7/1/32 | BB | 300000 | 300357 |

---

<br>Tax-Free High Yield Fund 27

------

---

| | | | |
|:---|:---|:---|:---|
| **MUNICIPAL BONDS AND NOTES (102.9%)\*** *cont.* | **Rating\*\*** | **Principal amount** | **Value** |
| **New Jersey** *cont.* | **New Jersey** *cont.* | **New Jersey** *cont.* | **New Jersey** *cont.* |
| NJ State Econ. Dev. Auth. Rev. Bonds |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;(Continental Airlines, Inc.), 5.50%, 6/1/33 | Ba3 | $2000000 | $2025775 |
| &nbsp;&nbsp;&nbsp;&nbsp;(Paterson Charter School), Ser. C, 5.30%, 7/1/44 | BB | 2250000 | 2249894 |
| &nbsp;&nbsp;&nbsp;&nbsp;(Portal North Bridge), 5.25%, 11/1/42 | A3 | 7300000 | 8002831 |
| &nbsp;&nbsp;&nbsp;&nbsp;(North Star Academy Charter School of Newark, Inc.), 5.00%, 7/15/47 | BBB- | 500000 | 508241 |
| &nbsp;&nbsp;&nbsp;&nbsp;Ser. EEE, 5.00%, 6/15/43 (Prerefunded 12/15/28) | AAA/P | &nbsp;&nbsp;&nbsp;&nbsp;1450000 | 1679437 |
| &nbsp;&nbsp;&nbsp;&nbsp;Ser. EEE, 5.00%, 6/15/43 | A3 | &nbsp;&nbsp;&nbsp;&nbsp;2460000 | 2569969 |
| &nbsp;&nbsp;&nbsp;&nbsp;Ser. EEE, 5.00%, 6/15/38 (Prerefunded 12/15/28) | A3 | 2500000 | 2895583 |
| &nbsp;&nbsp;&nbsp;&nbsp;(Provident Group-Montclair State U. Student Hsg. & Properties), 5.00%, 6/1/37 | AA | 1000000 | 1048499 |
| &nbsp;&nbsp;&nbsp;&nbsp;(North Star Academy Charter School of Newark, Inc.), 5.00%, 7/15/32 | BBB- | 1000000 | 1056515 |
| NJ State Econ. Dev. Auth. Energy Fac. Rev. Bonds, (UMM Energy Partners, LLC), Ser. A, 5.00%, 6/15/37 | Baa2 | 1000000 | 1000509 |
| NJ State Econ. Dev. Auth. Fac. Rev. Bonds, (Continental Airlines, Inc.), 5.625%, 11/15/30 | Ba3 | 1000000 | 1024027 |
| NJ State Hlth. Care Fac. Fin. Auth. VRDN, (Virtua Hlth.), Ser. C, 0.45%, 7/1/43 | A-1 | 2000000 | 2000000 |
| NJ State Trans. Trust Fund Auth. Rev. Bonds, Ser. BB, 5.00%, 6/15/34 | A3 | 575000 | 656005 |
|  |  |  | **30852346** |
| **New Mexico (0.1%)** | **New Mexico (0.1%)** | **New Mexico (0.1%)** | **New Mexico (0.1%)** |
| Sante Fe, Retirement Fac. Rev. Bonds, (El Castillo Retirement Residences), Ser. A, 5.00%, 5/15/49 | BB+/F | 1200000 | 1019776 |
|  |  |  | **1019776** |
| **New York (6.7%)** | **New York (6.7%)** | **New York (6.7%)** | **New York (6.7%)** |
| NY City, Muni. Wtr. & Swr. Syst. Fin. Auth. VRDN, 1.15%, 6/15/49 | VMIG 1 | 3990000 | 3990000 |
| NY City, Transitional Fin. Auth. Rev. Bonds. Ser. B-1, 4.00%, 11/1/41 <sup>T</sup> | AA+ | 10000000 | 10995288 |
| NY Counties, Tobacco Trust VI Rev. Bonds, (Tobacco Settlement Pass Through), Ser. A-2B, 5.00%, 6/1/51 | BB+/P | 2500000 | 2415342 |
| NY State Env. Fac. Corp. Solid Waste Disp. Mandatory Put Bonds (9/2/25), (Casella Waste Syst., Inc.), Ser. R-1, 2.75%, 9/1/50 | B+ | 475000 | 451926 |
| NY State Liberty Dev. Corp. 144A Rev. Bonds, (World Trade Ctr.), Class 2, 5.375%, 11/15/40 | BB-/P | 1250000 | 1251470 |
| NY State Thruway Auth. Personal Income Tax Rev. Bonds, Ser. C, 5.00%, 03/15/54 <sup>T</sup> | AA+ | 7300000 | 7981959 |
| NY State Trans. Special Fac. Dev. Corp. Rev. Bonds |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;(Delta Air Lines, Inc.), 5.00%, 10/1/40 | Baa3 | 2000000 | 2047162 |
| &nbsp;&nbsp;&nbsp;&nbsp;(American Airlines, Inc.), 3.00%, 8/1/31 | B/F | 1150000 | 1063430 |
| NY State, Liberty Dev. Corp. Rev. Bonds, (4 World Trade Ctr.), 3.00%, 11/15/51 | A+ | 8675000 | 6470770 |
| Port Auth. of NY & NJ Rev. Bonds |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;Ser. 218, 5.00%, 11/1/49 <sup>T</sup> | AA- | 4485000 | 4708892 |
| &nbsp;&nbsp;&nbsp;&nbsp;5.00%, 1/15/47 | Aa3 | 4300000 | 4625984 |
| Suffolk, Tobacco Asset Securitization Corp. Rev. Bonds, Ser. A-2, 4.00%, 6/1/50 | BBB+ | 1700000 | 1552026 |
|  |  |  | **47554249** |

---

<br>28 Tax-Free High Yield Fund

------

---

| | | | |
|:---|:---|:---|:---|
| **MUNICIPAL BONDS AND NOTES (102.9%)\*** *cont.* | **Rating\*\*** | **Principal amount** | **Value** |
| **North Carolina (1.5%)** | **North Carolina (1.5%)** | **North Carolina (1.5%)** | **North Carolina (1.5%)** |
| NC State Med. Care Comm. Hlth. Care Fac. Rev. Bonds, (Lutheran Svcs. for the Aging, Inc. Oblig. Group), Ser. C |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;4.00%, 3/1/42 | BB/P | $2500000 | $1996995 |
| &nbsp;&nbsp;&nbsp;&nbsp;4.00%, 3/1/31 | BB/P | 825000 | 758277 |
| &nbsp;&nbsp;&nbsp;&nbsp;4.00%, 3/1/30 | BB/P | 790000 | 737082 |
| NC State Med. Care Comm. Hlth. Fac. Rev. Bonds, (Presbyterian Homes Oblig. Group), 4.00%, 10/1/50 | BBB+/F | 1350000 | 1105137 |
| NC State Med. Care Comm. Retirement Fac. Rev. Bonds |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;(Maryfield, Inc. Oblig. Group), 5.00%, 10/1/50 | BB/P | 1500000 | 1395932 |
| &nbsp;&nbsp;&nbsp;&nbsp;(Twin Lakes Cmnty.), Ser. A, 5.00%, 1/1/49 | BBB/F | 2970000 | 2919037 |
| &nbsp;&nbsp;&nbsp;&nbsp;(Southminister, Inc.), 5.00%, 10/1/37 | BB/P | 1625000 | 1567589 |
|  |  |  | **10480049** |
| **Ohio (4.3%)** | **Ohio (4.3%)** | **Ohio (4.3%)** | **Ohio (4.3%)** |
| Buckeye, Tobacco Settlement Fin. Auth. Rev. Bonds |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;Ser. B-2, Class 2, 5.00%, 6/1/55 | BB/P | 9770000 | 9330385 |
| &nbsp;&nbsp;&nbsp;&nbsp;Ser. A-2, Class 1, 3.00%, 6/1/48 | BBB+ | 4870000 | 3711181 |
| Centerville, Hlth. Care Rev. Bonds, (Graceworks Lutheran Svcs.), 5.25%, 11/1/47 | BB+/P | 2000000 | 1839031 |
| Cleveland-Cuyahoga Cnty., Port Auth. Cultural Fac. Rev. Bonds |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;(Playhouse Square Foundation), 5.50%, 12/1/43 | BB+ | 500000 | 516042 |
| &nbsp;&nbsp;&nbsp;&nbsp;(Playhouse Sq. Foundation), 5.25%, 12/1/38 | BB+ | 1065000 | 1095046 |
| Hickory Chase, Cmnty. Auth. Infrastructure Impt. 144A Rev. Bonds, (Hickory Chase), Ser. A, 5.00%, 12/1/40 | B+/P | 1425000 | 1319234 |
| OH State Air Quality Dev. Auth. Exempt Fac. 144A Rev. Bonds, (Pratt Paper, LLC), 4.50%, 1/15/48 | BB+/P | 2000000 | 1896507 |
| OH State Higher Edl. Fac. Comm. Rev. Bonds |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;(Capital U.), 6.00%, 9/1/52 | BBB- | 1475000 | 1548907 |
| &nbsp;&nbsp;&nbsp;&nbsp;(Cleveland Inst. of Music (The)), 5.375%, 12/1/52 | BBB- | 2950000 | 3076511 |
| &nbsp;&nbsp;&nbsp;&nbsp;5.25%, 12/1/48 | BB | 750000 | 720250 |
| &nbsp;&nbsp;&nbsp;&nbsp;(Cleveland Inst. of Music (The)), 5.125%, 12/1/42 | BBB- | 3490000 | 3635006 |
| Southeastern OH Port Auth. Hosp. Fac. Rev. Bonds, (Memorial Hlth. Syst. Oblig. Group), 5.50%, 12/1/43 | B+/F | 235000 | 236958 |
| Washington Cnty, Hosp. Rev. Bonds, (Marietta Area Hlth. Care, Inc.), 6.75%, 12/1/52 | B+/P | 1500000 | 1524443 |
|  |  |  | **30449501** |
| **Oregon (2.4%)** | **Oregon (2.4%)** | **Oregon (2.4%)** | **Oregon (2.4%)** |
| Clackamas Cnty., Hosp. Fac. Auth. Rev. Bonds, (Rose Villa, Inc.), Ser. A, 5.375%, 11/15/55 | BB/P | 1000000 | 930969 |
| Port of Portland, Arpt. Rev. Bonds, Ser. 27A, 4.00%, 07/01/50 <sup>T</sup> | AA- | 15710000 | 15081735 |
| Warm Springs, Reservation Confederated Tribes 144A Rev. Bonds, (Pelton-Round Butte), Ser. B |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;5.00%, 11/1/39 | A3 | 700000 | 767554 |
| &nbsp;&nbsp;&nbsp;&nbsp;5.00%, 11/1/32 | A3 | 360000 | 407827 |
|  |  |  | **17188085** |

---

<br>Tax-Free High Yield Fund 29

------

---

| | | | |
|:---|:---|:---|:---|
| **MUNICIPAL BONDS AND NOTES (102.9%)\*** *cont.* | **Rating\*\*** | **Principal amount** | **Value** |
| **Pennsylvania (3.6%)** | **Pennsylvania (3.6%)** | **Pennsylvania (3.6%)** | **Pennsylvania (3.6%)** |
| Chester Cnty., Indl. Dev. Auth. Rev. Bonds |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;(Collegium Charter School), Ser. A, 5.125%, 10/15/37 | BB | $1200000 | $1198065 |
| &nbsp;&nbsp;&nbsp;&nbsp;(Renaissance Academy Charter School), 5.00%, 10/1/34 | BBB- | 625000 | 630469 |
| Chester Cnty., Indl. Dev. Auth. Student Hsg. Rev. Bonds, (West Chester U. Student Hsg., LLC), Ser. A, 5.00%, 8/1/45 | Ba2 | 2200000 | 2144824 |
| Cumberland Cnty., Muni. Auth. Rev. Bonds, (Asbury PA Obligated Group), 5.00%, 1/1/45 | BB+/P | 1000000 | 903716 |
| Dallas, Area Muni. Auth. U. Rev. Bonds, (Misericordia U.), 5.00%, 5/1/48 | Baa3 | 3000000 | 2954112 |
| Lancaster Cnty., Hosp. Auth. Hlth. Care Fac. Rev. Bonds, (Moravian Manors, Inc.), Ser. A, 5.00%, 6/15/49 | BB+/F | 4705000 | 4258137 |
| Lancaster, Indl. Dev. Auth. Rev. Bonds, (Willow Valley Communities) |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;5.00%, 12/1/49 | A/F | 2300000 | 2402228 |
| &nbsp;&nbsp;&nbsp;&nbsp;5.00%, 12/1/44 | A/F | 1850000 | 1946223 |
| &nbsp;&nbsp;&nbsp;&nbsp;4.00%, 12/1/44 | A/F | 1150000 | 1133424 |
| Montgomery Cnty., Indl. Auth. Rev. Bonds, (Whitemarsh Continuing Care Retirement Cmnty.), Ser. A, 5.25%, 1/1/48 | BB-/P | 1500000 | 1377137 |
| Moon, Indl. Dev. Auth. Rev. Bonds, (Baptist Homes Society Oblig. Group), 5.75%, 7/1/35 | B+/P | 850000 | 776582 |
| PA State Econ. Dev. Fin. Auth. Rev. Bonds, (PennDOT Major Bridges), 6.00%, 6/30/61 | Baa2 | 2500000 | 2778124 |
| PA State Higher Edl. Fac. Auth. Student Hsg. Rev. Bonds, (U. Properties, Inc.-East Stroudsburg), Ser. A, 5.00%, 7/1/31 | Baa3 | 1000000 | 1011835 |
| Philadelphia Auth. For Ind. Dev. 144A Rev. Bonds, (String Theory Charter School), 5.00%, 6/15/50 | BB+ | 1000000 | 962443 |
| Wilkes-Barre, Fin. Auth. Rev. Bonds, (Wilkes U.), 4.00%, 3/1/42 | BBB- | 1165000 | 1017019 |
|  |  |  | **25494338** |
| **Puerto Rico (2.0%)** | **Puerto Rico (2.0%)** | **Puerto Rico (2.0%)** | **Puerto Rico (2.0%)** |
| Cmnwlth. of PR, G.O. Bonds, Ser. A-1, 4.00%, 7/1/46 | BB/P | 3000000 | 2512118 |
| Cmnwlth. of PR, Sales Tax Fin. Corp. Rev. Bonds |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;Ser. A-1, 5.00%, 7/1/58 | BB-/P | 8997000 | 8886775 |
| &nbsp;&nbsp;&nbsp;&nbsp;Ser. A-2, 4.784%, 7/1/58 | B/P | 240000 | 229510 |
| &nbsp;&nbsp;&nbsp;&nbsp;Ser. A-1, 4.75%, 7/1/53 | B/P | 433000 | 412903 |
| &nbsp;&nbsp;&nbsp;&nbsp;Ser. A-1, 4.55%, 7/1/40 | B/P | 59000 | 58174 |
| &nbsp;&nbsp;&nbsp;&nbsp;Ser. A-2, 4.536%, 7/1/53 | B/P | 17000 | 15649 |
| &nbsp;&nbsp;&nbsp;&nbsp;Ser. A-1, 4.50%, 7/1/34 | B/P | 116000 | 116557 |
| &nbsp;&nbsp;&nbsp;&nbsp;Ser. A-2, 4.329%, 7/1/40 | B/P | 600000 | 575894 |
| &nbsp;&nbsp;&nbsp;&nbsp;Ser. A-1, zero %, 7/1/51 | B/P | 1236000 | 258349 |
| &nbsp;&nbsp;&nbsp;&nbsp;Ser. A-1, zero %, 7/1/46 | B/P | 1518000 | 418751 |
| &nbsp;&nbsp;&nbsp;&nbsp;Ser. A-1, zero %, 7/1/33 | B/P | 159000 | 96449 |
| &nbsp;&nbsp;&nbsp;&nbsp;Ser. A-1, zero %, 7/1/31 | B/P | 141000 | 95143 |
| &nbsp;&nbsp;&nbsp;&nbsp;Ser. A-1, zero %, 7/1/29 | B/P | 109000 | 81693 |
| &nbsp;&nbsp;&nbsp;&nbsp;Ser. A-1, zero %, 7/1/27 | B/P | 112000 | 92489 |
| &nbsp;&nbsp;&nbsp;&nbsp;Ser. A-1, zero %, 7/1/24 | B/P | 46000 | 43357 |
|  |  |  | **13893811** |

---

<br>30 Tax-Free High Yield Fund

------

---

| | | | |
|:---|:---|:---|:---|
| **MUNICIPAL BONDS AND NOTES (102.9%)\*** *cont.* | **Rating\*\*** | **Principal amount** | **Value** |
| **Rhode Island (0.4%)** | **Rhode Island (0.4%)** | **Rhode Island (0.4%)** | **Rhode Island (0.4%)** |
| Tobacco Settlement Fin. Corp. Rev. Bonds, Ser. B, 5.00%, 6/1/50 | BBB-/P | $3000000 | $3020244 |
|  |  |  | **3020244** |
| **South Carolina (0.9%)** | **South Carolina (0.9%)** | **South Carolina (0.9%)** | **South Carolina (0.9%)** |
| Berkeley Cnty., Assmt. Rev. Bonds, (Nexton Impt. Dist.), 4.25%, 11/1/40 | BB-/P | 1000000 | 872798 |
| SC State Jobs Econ. Dev. Auth. Edl. Fac. 144A Rev. Bonds |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;(High Point Academy), Ser. A, 5.75%, 6/15/39 | Ba1 | 2000000 | 2054169 |
| &nbsp;&nbsp;&nbsp;&nbsp;(Greenville Renewable Energy Ed. Charter School), 4.00%, 6/1/56 | BB/P | 1530000 | 1107940 |
| &nbsp;&nbsp;&nbsp;&nbsp;(Greenville Renewable Energy Ed. Charter School), 4.00%, 6/1/36 | BB/P | 1000000 | 875916 |
| SC State Jobs-Econ. Dev. Auth. Rev. Bonds, (Woodlands at Furman), Ser. A |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;5.00%, 11/15/54 | BB/P | 1000000 | 881766 |
| &nbsp;&nbsp;&nbsp;&nbsp;5.00%, 11/15/42 | BB/P | 585000 | 547270 |
|  |  |  | **6339859** |
| **Tennessee (1.7%)** | **Tennessee (1.7%)** | **Tennessee (1.7%)** | **Tennessee (1.7%)** |
| Chattanooga, Hlth. Edl. & Hsg. Fac. Rev. Bonds, (CommonSpirit Health Oblig. Group) |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;Ser. A-2, 5.00%, 8/1/49 <sup>T</sup> | A- | 725000 | 747152 |
| &nbsp;&nbsp;&nbsp;&nbsp;Ser. A-2, 5.00%, 8/1/44 <sup>T</sup> | A- | 425000 | 442680 |
| &nbsp;&nbsp;&nbsp;&nbsp;Ser. A-1, 4.00%, 8/1/44 <sup>T</sup> | A- | 850000 | 819055 |
| &nbsp;&nbsp;&nbsp;&nbsp;Ser. A-1, 4.00%, 8/1/38 <sup>T</sup> | A- | 425000 | 423232 |
| &nbsp;&nbsp;&nbsp;&nbsp;Ser. A-1, 4.00%, 8/1/37 <sup>T</sup> | A- | 425000 | 424776 |
| Metro. Govt. Nashville & Davidson Cnty., Hlth. & Edl. Fac. Board Rev. Bonds |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;(Trevecca Nazarene U.), 5.00%, 10/1/48 | BBB-/F | 1800000 | 1819396 |
| &nbsp;&nbsp;&nbsp;&nbsp;(Trevecca Nazarene U.), 5.00%, 10/1/39 | BBB-/F | 800000 | 818223 |
| &nbsp;&nbsp;&nbsp;&nbsp;(Trevecca Nazarene U.), 5.00%, 10/1/34 | BBB-/F | 400000 | 420434 |
| &nbsp;&nbsp;&nbsp;&nbsp;(Trevecca Nazarene U.), 5.00%, 10/1/29 | BBB-/F | 600000 | 629379 |
| &nbsp;&nbsp;&nbsp;&nbsp;(Blakeford at Green Hills), Ser. A, 4.00%, 11/1/55 | BBB-/F | 3000000 | 2338838 |
| Metro. Nashville, Arpt. Auth. Rev. Bonds, Ser. B |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;5.50%, 7/1/41 | A1 | 875000 | 986049 |
| &nbsp;&nbsp;&nbsp;&nbsp;5.50%, 7/1/38 | A1 | 875000 | 1000980 |
| Nashville, Metro. Dev. & Hsg. Agcy. 144A Tax Alloc. Bonds, (Fifth & Broadway Dev. Dist.), 5.125%, 6/1/36 | B+/P | 1250000 | 1278852 |
|  |  |  | **12149046** |
| **Texas (7.4%)** | **Texas (7.4%)** | **Texas (7.4%)** | **Texas (7.4%)** |
| Arlington, Higher Ed. Fin. Corp. Rev. Bonds |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;(Uplift Ed.), Ser. A, 5.00%, 12/1/36 | BBB- | 815000 | 841932 |
| &nbsp;&nbsp;&nbsp;&nbsp;(Wayside Schools), Ser. A, 4.00%, 8/15/46 | BB | 850000 | 684735 |
| &nbsp;&nbsp;&nbsp;&nbsp;(Wayside Schools), Ser. A, 4.00%, 8/15/36 | BB | 335000 | 296273 |
| Arlington, Higher Ed. Fin. Corp. 144A Rev. Bonds, (Magellan School (The)), 6.375%, 6/1/62 | Ba2 | 2400000 | 2413970 |
| Clifton, Higher Ed. Fin. Corp. Rev. Bonds |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;(Intl. Leadership), Ser. D, 6.125%, 8/15/48 | BB-/P | 6000000 | 6145862 |
| &nbsp;&nbsp;&nbsp;&nbsp;(IDEA Pub. Schools), Ser. A, 4.00%, 8/15/51 | A- | 3095000 | 2888504 |
| &nbsp;&nbsp;&nbsp;&nbsp;(IDEA Pub. Schools), Ser. A, 4.00%, 8/15/47 | A- | 4275000 | 4053145 |

---

<br>Tax-Free High Yield Fund 31

------

---

| | | | |
|:---|:---|:---|:---|
| **MUNICIPAL BONDS AND NOTES (102.9%)\*** *cont.* | **Rating\*\*** | **Principal amount** | **Value** |
| **Texas** *cont.* | **Texas** *cont.* | **Texas** *cont.* | **Texas** *cont.* |
| Harris Cnty., Cultural Ed. Fac. Fin. Corp. Rev. Bonds, (Brazos Presbyterian Homes, Inc.), 5.00%, 1/1/37 | BB+/F | $1000000 | $930598 |
| Houston, Arpt. Syst. Rev. Bonds |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;Ser. B-1, 5.00%, 7/15/35 | B | 200000 | 200560 |
| &nbsp;&nbsp;&nbsp;&nbsp;(United Airlines, Inc.), 4.00%, 7/1/41 | B-/F | 3750000 | 3380156 |
| Houston, Higher Ed. Fin. Corp. Rev. Bonds, (Houston Baptist U.), 4.00%, 10/1/51 | BBB- | 2100000 | 1780918 |
| Matagorda Cnty., Poll. Control Rev. Bonds, (Dist. No. 1), Ser. A, AMBAC, 4.40%, 5/1/30 | A- | 3000000 | 3175208 |
| New Hope, Cultural Ed. Fac. Fin. Corp. Rev. Bonds |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;(MRC Sr. Living-Langford (The)), Ser. A, 5.50%, 11/15/52 | B-/P | 250000 | 211485 |
| &nbsp;&nbsp;&nbsp;&nbsp;(MRC Senior Living-Langford (The)), 5.50%, 11/15/46 | B-/P | 700000 | 605903 |
| &nbsp;&nbsp;&nbsp;&nbsp;(Wesleyan Homes, Inc.), 5.50%, 1/1/43 | BB-/P | 1050000 | 926862 |
| &nbsp;&nbsp;&nbsp;&nbsp;(MRC Senior Living-Langford (The)), 5.375%, 11/15/36 | B-/P | 500000 | 456463 |
| &nbsp;&nbsp;&nbsp;&nbsp;(Collegiate Hsg.-Tarleton St.), 5.00%, 4/1/39 (Prerefunded 4/1/24) | AAA/P | 500000 | 514027 |
| &nbsp;&nbsp;&nbsp;&nbsp;(Woman's U.-Collegiate Hsg. Denton, LLC), Ser. A-1, AGM, 5.00%, 7/1/32 | AA | 700000 | 750199 |
| &nbsp;&nbsp;&nbsp;&nbsp;(Westminster Manor), 4.00%, 11/1/55 | BBB/F | 1450000 | 1105271 |
| &nbsp;&nbsp;&nbsp;&nbsp;(Woman's U.-Collegiate Hsg. Denton, LLC), Ser. A-1, AGM, 4.00%, 7/1/43 | AA | 1600000 | 1530230 |
| Tarrant Cnty., Cultural Ed. Fac. Fin. Corp. Retirement Fac. Rev. Bonds, (Buckner Retirement Svcs., Inc.), 5.00%, 11/15/37 | A/F | 1620000 | 1683871 |
| Temple, Tax Increment 144A Tax Alloc. Bonds, (Reinvestment Zone No. 1), Ser. A, 5.00%, 8/1/38 | Baa2 | 3500000 | 3561042 |
| TX Private Activity Surface Trans. Corp. Rev. Bonds, (Segment 3C), 5.00%, 6/30/58 | Baa2 | 4500000 | 4561338 |
| TX State Private Activity Bond Surface Trans. Corp. Rev. Bonds, (Blueridge Trans. Group, LLC (SH 288 Toll Lane)), 5.00%, 12/31/50 | Baa2 | 1750000 | 1756595 |
| TX State Tech. College Syst. Fin. Syst. Rev. Bonds, Ser. A, AGM, 6.00%, 8/1/54 | AA | 4000000 | 4731340 |
| TX State Trans. Comm. Rev. Bonds, (State Hwy. 249 Sys.), Ser. A, zero %, 8/1/39 | Baa3 | 1500000 | 668634 |
| Uptown Dev. Auth. Tax Alloc. Bonds, (City of Houston Reinvestment Zone No. 16) |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;3.00%, 9/1/40 | Baa2 | 605000 | 480558 |
| &nbsp;&nbsp;&nbsp;&nbsp;3.00%, 9/1/39 | Baa2 | 550000 | 444893 |
| &nbsp;&nbsp;&nbsp;&nbsp;3.00%, 9/1/38 | Baa2 | 750000 | 617817 |
| &nbsp;&nbsp;&nbsp;&nbsp;3.00%, 9/1/37 | Baa2 | 650000 | 544074 |
| &nbsp;&nbsp;&nbsp;&nbsp;3.00%, 9/1/36 | Baa2 | 650000 | 555541 |
|  |  |  | **52498004** |
| **Utah (0.9%)** | **Utah (0.9%)** | **Utah (0.9%)** | **Utah (0.9%)** |
| Infrastructure Agcy. Telecomm. Rev. Bonds |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;5.00%, 10/15/32 | BBB-/F | 1000000 | 1047787 |
| &nbsp;&nbsp;&nbsp;&nbsp;4.00%, 10/15/42 | BBB-/F | 1500000 | 1262571 |
| &nbsp;&nbsp;&nbsp;&nbsp;4.00%, 10/15/36 | BBB-/F | 1000000 | 899120 |

---

<br>32 Tax-Free High Yield Fund

------

---

| | | | |
|:---|:---|:---|:---|
| **MUNICIPAL BONDS AND NOTES (102.9%)\*** *cont.* | **Rating\*\*** | **Principal amount** | **Value** |
| **Utah** *cont.* | **Utah** *cont.* | **Utah** *cont.* | **Utah** *cont.* |
| MDA Mountain Village Pub. Infrastructure Dist. Special Assmt., Ser. A, 5.00%, 8/1/50 | B/P | $2000000 | $1827736 |
| Mida Mountain Village Pub. Infrastructure Dist. 144A Special Assmt. Bonds, (Mountain Village Assmt. Area No. 2), 4.00%, 8/1/50 | B/P | 1625000 | 1216501 |
|  |  |  | **6253715** |
| **Virginia (0.9%)** | **Virginia (0.9%)** | **Virginia (0.9%)** | **Virginia (0.9%)** |
| Cherry Hill Cmnty., Dev. Auth. 144A Special Assmt. Bonds, (Potomac Shores), 5.15%, 3/1/35 | B/P | 500000 | 501933 |
| Fairfax Cnty., Econ. Dev. Auth. Res. Care Fac. Rev. Bonds, (Goodwin House, Inc.), Ser. A, 5.00%, 10/1/42 (Prerefunded 10/1/24) | AAA/P | 350000 | 370024 |
| Farms of New Kent, Cmnty. Dev. Auth. 144A Special Assmt. Bonds, Ser. A, 3.75%, 3/1/36 | B+/P | 1370000 | 1306540 |
| James City Cnty., Econ. Dev. Auth. Rev. Bonds, (Williamsburg Landing), Ser. A, 4.00%, 12/1/50 | BB/P | 2000000 | 1498918 |
| Lower Magnolia Green Cmnty., Dev. Auth. 144A Special Assmt. Bonds, 5.00%, 3/1/35 | B/P | 835000 | 833466 |
| Suffolk, Econ. Dev. Auth. Retirement Fac. Rev. Bonds, (United Church Homes & Svcs. Oblig. Group), 5.00%, 9/1/31 | BB/P | 1500000 | 1458158 |
|  |  |  | **5969039** |
| **Washington (1.9%)** | **Washington (1.9%)** | **Washington (1.9%)** | **Washington (1.9%)** |
| Bellevue, G.O. Bonds, 4.00%, 12/1/37 | Aaa | 885000 | 927525 |
| Kalispel Tribe of Indians Priority Dist. Rev. Bonds, Ser. A, 5.00%, 1/1/32 | BB+/P | 990000 | 1034775 |
| Skagit Cnty., Pub. Hosp. Dist. No. 1 Rev. Bonds, (Skagit Regl. Hlth. Impt.), 5.00%, 12/1/37 | Baa3 | 2000000 | 2061956 |
| WA State Hsg. Fin. Comm. Rev. Bonds |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;(Wesley Homes Lea Hill), 5.00%, 7/1/36 | B/P | 575000 | 536561 |
| &nbsp;&nbsp;&nbsp;&nbsp;(Social Certif.), Ser. A-1, 3.50%, 12/20/35 | BBB+ | 3669497 | 3460797 |
| WA State Hsg. Fin. Comm. 144A Rev. Bonds, (Presbyterian Retirement Cmnty. Northwest), Ser. A, 5.00%, 1/1/46 | BB/F | 4000000 | 3293965 |
| WA State Hsg. Fin. Comm. Nonprofit 144A Rev. Bonds, (Spokane Intl. Academy), Ser. A |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;5.00%, 7/1/50 | Ba2 | 500000 | 476478 |
| &nbsp;&nbsp;&nbsp;&nbsp;4.00%, 7/1/40 | Ba2 | 2235000 | 1900359 |
|  |  |  | **13692416** |
| **Wisconsin (5.5%)** | **Wisconsin (5.5%)** | **Wisconsin (5.5%)** | **Wisconsin (5.5%)** |
| Pub. Fin. Auth. Rev. Bonds, (Northwest Nazarene U.), 5.00%, 10/1/43 | Baa3 | 3425000 | 3527958 |
| Pub. Fin. Auth. 144A Rev. Bonds |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;(WFCS Holdings II, LLC), Ser. A-1, 5.00%, 1/1/56 | BB/P | 2145000 | 1767356 |
| &nbsp;&nbsp;&nbsp;&nbsp;(Roseman U. of Hlth. Sciences), 5.00%, 4/1/50 | BB | 1800000 | 1700559 |
| Pub. Fin. Auth. Conference Ctr. & Hotel Rev. Bonds, (U. of NC Charlotte Foundation), Ser. A, 4.00%, 9/1/51 | BB+/P | 3500000 | 2801878 |

---

<br>Tax-Free High Yield Fund 33

------

---

| | | | |
|:---|:---|:---|:---|
| **MUNICIPAL BONDS AND NOTES (102.9%)\*** *cont.* | **Rating\*\*** | **Principal amount** | **Value** |
| **Wisconsin** *cont.* | **Wisconsin** *cont.* | **Wisconsin** *cont.* | **Wisconsin** *cont.* |
| Pub. Fin. Auth. Ed. 144A Rev. Bonds, (North Carolina Leadership Academy) |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;5.00%, 6/15/54 | BB+/P | $455000 | $414218 |
| &nbsp;&nbsp;&nbsp;&nbsp;5.00%, 6/15/49 | BB+/P | 1040000 | 961200 |
| &nbsp;&nbsp;&nbsp;&nbsp;5.00%, 6/15/39 | BB+/P | 410000 | 397933 |
| Pub. Fin. Auth. Edl. Fac. Rev. Bonds, (Piedmont Cmnty. Charter School), 5.00%, 6/15/53 | Baa3 | 1000000 | 1008115 |
| Pub. Fin. Auth. Exempt Fac. Rev. Bonds, (Celanese U.S. Holdings, LLC), Ser. C, 4.30%, 11/1/30 | Baa3 | 700000 | 685508 |
| Pub. Fin. Auth. Retirement Communities Rev. Bonds, (Evergreens Oblig. Group), Ser. A, 5.00%, 11/15/49 | BBB/F | 2000000 | 1962213 |
| Pub. Fin. Auth. Retirement Fac. 144A Rev. Bonds, (Southminster, Inc.), 5.00%, 10/1/48 | BB/F | 1500000 | 1299436 |
| Pub. Fin. Auth. Student Hsg. Fac. Rev. Bonds |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;(NC A&T Real Estate Foundation, LLC), Ser. B, 5.00%, 6/1/44 | BBB- | 1900000 | 1865644 |
| &nbsp;&nbsp;&nbsp;&nbsp;(Appalachian State U.), Ser. A, AGM, 4.00%, 7/1/59 | AA | 1350000 | 1206703 |
| &nbsp;&nbsp;&nbsp;&nbsp;(Appalachian State U.), Ser. A, AGM, 4.00%, 7/1/55 | AA | 1000000 | 904170 |
| Pub. Fin. Auth. Student Hsg. Fac. 144A Rev. Bonds, (UHF RISE Student Hsg., LLC), Ser. A-1, 4.00%, 7/1/61 | Ba1 | 1400000 | 1054922 |
| WI Pub. Fin. Auth. Edl. Fac. Rev. Bonds, (Queens U. of Charlotte), Ser. A, 5.25%, 3/1/42 | BBB | 3000000 | 3104069 |
| WI Pub. Fin. Auth. Hotel Rev. Bonds, (Grand Hyatt), 5.00%, 2/1/62 | BBB- | 4000000 | 3841593 |
| WI Pub. Fin. Auth. Hotel 144A Rev. Bonds, (Grand Hyatt), 6.00%, 2/1/62 | BB-/P | 2000000 | 1985284 |
| WI State Hlth. & Edl. Fac. Auth. Rev. Bonds |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;(Oakwood Lutheran Sr. Ministries Oblig. Group), 4.00%, 1/1/57 | BB/P | 1350000 | 974174 |
| &nbsp;&nbsp;&nbsp;&nbsp;(St. John's Communities, Inc.), 4.00%, 9/15/36 | BBB-/F | 790000 | 705389 |
| &nbsp;&nbsp;&nbsp;&nbsp;(St. John's Communities, Inc.), 4.00%, 9/15/31 | BBB-/F | 970000 | 908527 |
| &nbsp;&nbsp;&nbsp;&nbsp;(St. John's Communities, Inc.), 4.00%, 9/15/30 | BBB-/F | 935000 | 886548 |
| WI State Pub. Fin. Auth Sr. Living Rev. Bonds, (Rose Villa, Inc.), Ser. A |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;6.00%, 11/15/49 (Prerefunded 11/15/24) | BB-/P | 1000000 | 1054117 |
| &nbsp;&nbsp;&nbsp;&nbsp;5.50%, 11/15/34 (Prerefunded 11/15/24) | BB-/P | 1685000 | 1762528 |
| WI State Pub. Fin. Auth Sr. Living 144A Rev. Bonds, (Rose Villa, Inc.), Ser. A, 5.75%, 11/15/44 (Prerefunded 11/15/24) | BB-/P | 500000 | 525166 |
| WI State Pub. Fin. Auth. 144A Rev. Bonds, (Church Home of Hartford, Inc.), Ser. A, 5.00%, 9/1/38 | BB/F | 1500000 | 1382264 |
|  |  |  | **38687472** |
| **Total municipal bonds and notes (cost $762,723,820)** | **Total municipal bonds and notes (cost $762,723,820)** | **Total municipal bonds and notes (cost $762,723,820)** | **$726248669** |

---

---

| | | |
|:---|:---|:---|
| **UNITIZED TRUST (0.0%)\*** | **Shares** | **Value** |
| CMS Liquidating Trust 144A <sup>F</sup> | 400 | $10368 |
| **Total unitized trust (cost $—)** | **Total unitized trust (cost $—)** | **$10368** |

---

<br>34 Tax-Free High Yield Fund

------

---

| | | | |
|:---|:---|:---|:---|
| **SHORT-TERM INVESTMENTS (2.1%)\*** | **SHORT-TERM INVESTMENTS (2.1%)\*** | **Principal amount/<br>shares** | **Value** |
| Putnam Short Term Investment Fund Class P 4.58% <sup>L</sup> | Shares | 13242148 | 13242148 |
| U.S. Treasury Bills 4.491%, 3/16/23 <sup>#</sup> |  | $600000 | $596798 |
| U.S. Treasury Bills 4.530%, 3/2/23 <sup>#</sup> |  | 400000 | 398577 |
| U.S. Treasury Bills 4.410%, 2/23/23 <sup>#</sup> |  | 300000 | 299184 |
| **Total short-term investments (cost $14,536,769)** | **Total short-term investments (cost $14,536,769)** | **Total short-term investments (cost $14,536,769)** | **$14536707** |

---

---

| | |
|:---|:---|
| **TOTAL INVESTMENTS** | **TOTAL INVESTMENTS** |
| **Total investments (cost $777,260,589)** | **$740795744** |

---

---

| | |
|:---|:---|
| **Notes to the fund's portfolio** | **Notes to the fund's portfolio** |
|  | Unless noted otherwise, the notes to the fund's portfolio are for the close of the fund's reporting period, which ran from August 1, 2022 through January 31, 2023 (the reporting period). Within the following notes to the portfolio, references to "Putnam Management" represent Putnam Investment Management, LLC, the fund's manager, an indirect wholly-owned subsidiary of Putnam Investments, LLC and references to "ASC 820" represent Accounting Standards Codification 820 Fair Value Measurements and Disclosures. |
| <sup>\*</sup> | Percentages indicated are based on net assets of $705,443,055. |
| <sup>\*\*</sup> | The Moody's, Standard & Poor's or Fitch ratings indicated are believed to be the most recent ratings available at the close of the reporting period for the securities listed. Ratings are generally ascribed to securities at the time of issuance. While the agencies may from time to time revise such ratings, they undertake no obligation to do so, and the ratings do not necessarily represent what the agencies would ascribe to these securities at the close of the reporting period. Securities rated by Fitch are indicated by "/F." Securities rated by Putnam are indicated by "/P." The Putnam rating categories are comparable to the Standard & Poor's classifications. If a security is insured, it will usually be rated by the ratings organizations based on the financial strength of the insurer. For further details regarding security ratings, please see the Statement of Additional Information. |
| <sup>†</sup> | This security is non-income-producing. |
| <sup>††</sup> | The interest rate and date shown parenthetically represent the new interest rate to be paid and the date the fund will begin accruing interest at this rate. |
| <sup>#</sup> | This security, in part or in entirety, was pledged and segregated with the broker to cover margin requirements for futures contracts at the close of the reporting period. Collateral at period end totaled $1,235,521 and is included in Investments in securities on the Statement of assets and liabilities (Notes 1 and 8). |
| <sup>F</sup> | This security is valued by Putnam Management at fair value following procedures approved by the Trustees. Securities are classified as Level 3 for ASC 820 based on the securities' valuation inputs (Note 1). |
| <sup>L</sup> | Affiliated company (Note 5). The rate quoted in the security description is the annualized 7-day yield of the fund at the close of the reporting period. |
| <sup>T</sup> | Underlying security in a tender option bond transaction. This security has been segregated as collateral for financing transactions. |
|  | Unless otherwise noted, the rates quoted in Short-term investments security descriptions represent the weighted average yield to maturity. |
|  | 144A after the name of an issuer represents securities exempt from registration under Rule 144A of the Securities Act of 1933, as amended. These securities may be resold in transactions exempt from registration, normally to qualified institutional buyers. |
|  | On Mandatory Put Bonds, the rates shown are the current interest rates at the close of the reporting period and the dates shown represent the next mandatory put dates. Rates are set by remarketing agents and may take into consideration market supply and demand, credit quality and the current SIFMA Municipal Swap Index, 1 Month US LIBOR or 3 Month US LIBOR rates, which were 1.66%, 4.57% and 4.81%, respectively, as of the close of the reporting period. |
|  | The dates shown parenthetically on prerefunded bonds represent the next prerefunding dates. |
|  | The dates shown on debt obligations are the original maturity dates. |

---

<br>Tax-Free High Yield Fund 35

------

---

| | |
|:---|:---|
| The fund had the following sector concentrations greater than 10% at the close of the reporting period (as a percentage of net assets): | The fund had the following sector concentrations greater than 10% at the close of the reporting period (as a percentage of net assets): |
| Education | 25.7% |
| Health care | 18.3 |
| Transportation | 11.7 |

---

---

| | | | | | |
|:---|:---|:---|:---|:---|:---|
| **FUTURES CONTRACTS OUTSTANDING at 1/31/23 (Unaudited)** | **FUTURES CONTRACTS OUTSTANDING at 1/31/23 (Unaudited)** | **FUTURES CONTRACTS OUTSTANDING at 1/31/23 (Unaudited)** | **FUTURES CONTRACTS OUTSTANDING at 1/31/23 (Unaudited)** | **FUTURES CONTRACTS OUTSTANDING at 1/31/23 (Unaudited)** | **FUTURES CONTRACTS OUTSTANDING at 1/31/23 (Unaudited)** |
| | **Number of<br>contracts** | **Notional<br>amount** | **Value** | &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;**Expiration<br>date** | **Unrealized<br>appreciation/<br>(depreciation)** |
| U.S. Treasury Note 5 yr (Short) | 160 | $17478750 | $17478750 | &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Mar-23 | $2140 |
| U.S. Treasury Note Ultra 10 yr (Short) | 343 | 41572672 | 41572672 | &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Mar-23 | (721006) |
| **Unrealized appreciation** | **Unrealized appreciation** |  |  |  | **2140** |
| **Unrealized (depreciation)** | **Unrealized (depreciation)** |  |  |  | **(721006)** |
| **Total** | **Total** | **Total** | **Total** | **Total** | **$(718866)** |

---

ASC 820 establishes a three-level hierarchy for disclosure of fair value measurements. The valuation hierarchy is based upon the transparency of inputs to the valuation of the fund's investments. The three levels are defined as follows:

Level 1: Valuations based on quoted prices for identical securities in active markets.

Level 2: Valuations based on quoted prices in markets that are not active or for which all significant inputs are observable, either directly or indirectly.

Level 3: Valuations based on inputs that are unobservable and significant to the fair value measurement.

The following is a summary of the inputs used to value the fund's net assets as of the close of the reporting period:

---

| | | | |
|:---|:---|:---|:---|
| | | **Valuation inputs** | **Valuation inputs** |
| **Investments in securities:** | **Level 1** | **Level 2** | **Level 3** |
| Municipal bonds and notes | $— | $726248669 | $— |
| Unitized trust |  |  | 10368 |
| Short-term investments |  | 14536707 |  |
| **Totals by level** | **$—** | **$740785376** | **$10368** |

---

---

| | | | |
|:---|:---|:---|:---|
| | | **Valuation inputs** | **Valuation inputs** |
| **Other financial instruments:** | **Level 1** | **Level 2** | **Level 3** |
| Futures contracts | $(718866) | $— | $— |
| **Totals by level** | **$(718866)** | **$—** | **$—** |
| At the start and close of the reporting period, Level 3 investments in securities represented less than 1% of the fund's net assets and were not considered a significant portion of the fund's portfolio. | At the start and close of the reporting period, Level 3 investments in securities represented less than 1% of the fund's net assets and were not considered a significant portion of the fund's portfolio. | At the start and close of the reporting period, Level 3 investments in securities represented less than 1% of the fund's net assets and were not considered a significant portion of the fund's portfolio. | At the start and close of the reporting period, Level 3 investments in securities represented less than 1% of the fund's net assets and were not considered a significant portion of the fund's portfolio. |

---

The accompanying notes are an integral part of these financial statements.

<br>36 Tax-Free High Yield Fund

------

**Statement of assets and liabilities** 1/31/23 (Unaudited)

---

| | |
|:---|:---|
| **ASSETS** |  |
| Investment in securities, at value (Notes 1 and 8): |  |
| Unaffiliated issuers (identified cost $764,018,441) | $727553596 |
| Affiliated issuers (identified cost $13,242,148) (Note 5) | 13242148 |
| Interest and other receivables | 7762222 |
| Receivable for shares of the fund sold | 439537 |
| Receivable for investments sold | 3559996 |
| Prepaid assets | 60534 |
| **Total assets** | **752618033** |
| **LIABILITIES** |  |
| Payable for investments purchased | 8325981 |
| Payable for shares of the fund repurchased | 774898 |
| Payable for compensation of Manager (Note 2) | 278845 |
| Payable for custodian fees (Note 2) | 6113 |
| Payable for investor servicing fees (Note 2) | 85411 |
| Payable for Trustee compensation and expenses (Note 2) | 291816 |
| Payable for administrative services (Note 2) | 1326 |
| Payable for distribution fees (Note 2) | 123481 |
| Payable for floating rate notes issued (Note 1) | 36878184 |
| Payable for variation margin on futures contracts (Note 1) | 108784 |
| Distributions payable to shareholders | 219734 |
| Other accrued expenses | 80405 |
| **Total liabilities** | **47174978** |
| **Net assets** | **$705443055** |
| **REPRESENTED BY** |  |
| Paid-in capital (Unlimited shares authorized) (Notes 1 and 4) | $747163796 |
| Total distributable earnings (Note 1) | (41720741) |
| **Total — Representing net assets applicable to capital shares outstanding** | **$705443055** |
| **COMPUTATION OF NET ASSET VALUE AND OFFERING PRICE** |  |
| **Net asset value and redemption price per class A share** |  |
| ($521,248,997 divided by 45,560,867 shares) | $11.44 |
| **Offering price per class A share** (100/96.00 of $11.44)<sup>\*</sup> | $11.92 |
| **Net asset value and offering price per class B share** ($905,531 divided by 78,936 shares)<sup>\*\*</sup> | $11.47 |
| **Net asset value and offering price per class C share** ($15,676,918 divided by 1,366,278 shares)<sup>\*\*</sup> | $11.47 |
| **Net asset value, offering price and redemption price per class R6 share** |  |
| ($1,814,853 divided by 157,829 shares) | $11.50 |
| **Net asset value, offering price and redemption price per class Y share** |  |
| ($165,796,756 divided by 14,425,655 shares) | $11.49 |

---

<sup>\*</sup> On single retail sales of less than $50,000. On sales of $50,000 or more the offering price is reduced.

<sup>\*\*</sup> Redemption price per share is equal to net asset value less any applicable contingent deferred sales charge.

The accompanying notes are an integral part of these financial statements.

Tax-Free High Yield Fund 37

------

**Statement of operations** Six months ended 1/31/23 (Unaudited)

---

| | |
|:---|:---|
| **INVESTMENT INCOME** |  |
| Interest (including interest income of $228,026 from investments in affiliated issuers) (Note 5) | $16408254 |
| **Total investment income** | **16408254** |
| **EXPENSES** |  |
| Compensation of Manager (Note 2) | 1644499 |
| Investor servicing fees (Note 2) | 262292 |
| Custodian fees (Note 2) | 10210 |
| Trustee compensation and expenses (Note 2) | 15613 |
| Distribution fees (Note 2) | 743339 |
| Administrative services (Note 2) | 15086 |
| Interest and fee expense (Note 1) | 479079 |
| Other | 163597 |
| **Total expenses** | **3333715** |
| Expense reduction (Note 2) | (2167) |
| **Net expenses** | **3331548** |
| **Net investment income** | **13076706** |
| **REALIZED AND UNREALIZED GAIN (LOSS)** |  |
| **Net realized gain (loss) on:** |  |
| Securities from unaffiliated issuers (Notes 1 and 3) | (6140744) |
| Futures contracts (Note 1) | 2067919 |
| Swap contracts (Note 1) | 724950 |
| **Total net realized loss** | **(3347875)** |
| **Change in net unrealized appreciation (depreciation) on:** |  |
| Securities from unaffiliated issuers | (13246816) |
| Futures contracts | (610502) |
| Swap contracts | (833156) |
| **Total change in net unrealized depreciation** | **(14690474)** |
| **Net loss on investments** | **(18038349)** |
| **Net decrease in net assets resulting from operations** | **$(4961643)** |

---

The accompanying notes are an integral part of these financial statements.

38 Tax-Free High Yield Fund

------

**Statement of changes in net assets**

---

| | | |
|:---|:---|:---|
| **DECREASE IN NET ASSETS** | **Six months ended 1/31/23\*** | **Year ended 7/31/22** |
| **Operations** |  |  |
| Net investment income | $13076706 | $24717255 |
| Net realized loss on investments | (3347875) | (824252) |
| Change in net unrealized depreciation of investments | (14690474) | (105146111) |
| **Net decrease in net assets resulting from operations** | **(4961643)** | **(81253108)** |
| Distributions to shareholders (Note 1): |  |  |
| From ordinary income |  |  |
| Taxable net investment income |  |  |
| Class A | (390541) | (165977) |
| Class B | (682) | (522) |
| Class C | (12123) | (5680) |
| Class R6 | (1341) | (492) |
| Class Y | (121769) | (47190) |
| Net realized short-term gain on investments |  |  |
| Class A |  | (374304) |
| Class B |  | (1273) |
| Class C |  | (13158) |
| Class R6 |  | (1043) |
| Class Y |  | (110925) |
| From tax-exempt net investment income |  |  |
| Class A | (9375979) | (18463887) |
| Class B | (16478) | (48188) |
| Class C | (229958) | (482701) |
| Class R6 | (35311) | (57121) |
| Class Y | (2933750) | (5608836) |
| From net realized long-term gain on investments |  |  |
| Class A |  | (9264990) |
| Class B |  | (31469) |
| Class C |  | (325583) |
| Class R6 |  | (25832) |
| Class Y |  | (2744422) |
| Decrease from capital share transactions (Note 4) | (8901507) | (48153012) |
| **Total decrease in net assets** | **(26981082)** | **(167179713)** |
| **NET ASSETS** |  |  |
| Beginning of period | 732424137 | 899603850 |
| **End of period** | **$705443055** | **$732424137** |

---

<sup>\*</sup> Unaudited.

The accompanying notes are an integral part of these financial statements.

Tax-Free High Yield Fund 39

------

**Financial highlights**<br>(For a common share outstanding throughout the period)

---

| | | | | | | | | | | | | | |
|:---|:---|:---|:---|:---|:---|:---|:---|:---|:---|:---|:---|:---|:---|
|  | **INVESTMENT OPERATIONS** | **INVESTMENT OPERATIONS** | | | **LESS DISTRIBUTIONS** | **LESS DISTRIBUTIONS** | | | | **RATIOS AND SUPPLEMENTAL DATA** | **RATIOS AND SUPPLEMENTAL DATA** | **RATIOS AND SUPPLEMENTAL DATA** | |
|  |  |  |  |  |  |  |  |  |  |  |  | Ratio of net |  |
|  | **Net asset** |  | Net realized |  |  |  |  |  |  |  | Ratio | investment |  |
|  | **value,** |  | and unrealized | **Total from** | From net | From |  | **Net asset** | **Total return** | **Net assets,** | of expenses | income (loss) | Portfolio |
|  | **beginning** | Net investment | gain (loss) | **investment** | investment | net realized gain | **Total** | **value, end** | **at net asset** | **end of period** | to average | to average | turnover |
| Period ended | **of period** | income (loss) | on investments | **operations** | income | on investments | **distributions** | **of period** | **value (%)**<sup>a</sup> | **(in thousands)** | net assets (%)<sup>b</sup> | net assets (%) | (%) |
| **Class A** |  |  |  |  |  |  |  |  |  |  |  |  |  |
| January 31, 2023<sup>\*\*</sup> | **$11.70** | .21 | (.26) | **(.05)** | (.21) |  | **(.21)** | **$11.44** | **(.35)**<sup>\*</sup> | **$521249** | .50<sup>\*d</sup> | 1.87<sup>\*</sup> | 16<sup>\*</sup> |
| July 31, 2022 | **13.46** | .38 | (1.58) | **(1.20)** | (.37) | (.19) | **(.56)** | **11.70** | **(9.11)** | **564818** | .87<sup>d</sup> | 2.96 | 34 |
| July 31, 2021 | **12.67** | .40 | .79 | **1.19** | (.40) | —<sup>c</sup> | **(.40)** | **13.46** | **9.59** | **681458** | .85<sup>d</sup> | 3.08 | 25 |
| July 31, 2020 | **12.87** | .44 | (.07) | **.37** | (.44) | (.13) | **(.57)** | **12.67** | **2.95** | **658929** | .86<sup>d</sup> | 3.36 | 43 |
| July 31, 2019 | **12.49** | .45 | .40 | **.85** | (.47) |  | **(.47)** | **12.87** | **6.98** | **680689** | .84<sup>d</sup> | 3.59 | 47 |
| July 31, 2018 | **12.51** | .49 | (.02) | **.47** | (.49) |  | **(.49)** | **12.49** | **3.81** | **687025** | .82 | 3.71 | 39 |
| **Class B** |  |  |  |  |  |  |  |  |  |  |  |  |  |
| January 31, 2023<sup>\*\*</sup> | **$11.74** | .18 | (.28) | **(.10)** | (.17) |  | **(.17)** | **$11.47** | **(.74)**<sup>\*</sup> | **$906** | .80<sup>\*d</sup> | 1.55<sup>\*</sup> | 16<sup>\*</sup> |
| July 31, 2022 | **13.50** | .30 | (1.57) | **(1.27)** | (.30) | (.19) | **(.49)** | **11.74** | **(9.60)** | **1468** | 1.47<sup>d</sup> | 2.33 | 34 |
| July 31, 2021 | **12.71** | .32 | .80 | **1.12** | (.33) | —<sup>c</sup> | **(.33)** | **13.50** | **8.92** | **2639** | 1.45<sup>d</sup> | 2.50 | 25 |
| July 31, 2020 | **12.90** | .35 | (.05) | **.30** | (.36) | (.13) | **(.49)** | **12.71** | **2.34** | **4034** | 1.48<sup>d</sup> | 2.74 | 43 |
| July 31, 2019 | **12.51** | .38 | .40 | **.78** | (.39) |  | **(.39)** | **12.90** | **6.39** | **6297** | 1.46<sup>d</sup> | 2.98 | 47 |
| July 31, 2018 | **12.54** | .41 | (.03) | **.38** | (.41) |  | **(.41)** | **12.51** | **3.08** | **7834** | 1.44 | 3.09 | 39 |
| **Class C** |  |  |  |  |  |  |  |  |  |  |  |  |  |
| January 31, 2023<sup>\*\*</sup> | **$11.74** | .17 | (.27) | **(.10)** | (.17) |  | **(.17)** | **$11.47** | **(.81)**<sup>\*</sup> | **$15677** | .88<sup>\*d</sup> | 1.49<sup>\*</sup> | 16<sup>\*</sup> |
| July 31, 2022 | **13.51** | .29 | (1.59) | **(1.30)** | (.28) | (.19) | **(.47)** | **11.74** | **(9.79)** | **18207** | 1.62<sup>d</sup> | 2.20 | 34 |
| July 31, 2021 | **12.71** | .30 | .81 | **1.11** | (.31) | —<sup>c</sup> | **(.31)** | **13.51** | **8.84** | **24231** | 1.60<sup>d</sup> | 2.36 | 25 |
| July 31, 2020 | **12.90** | .33 | (.05) | **.28** | (.34) | (.13) | **(.47)** | **12.71** | **2.18** | **30283** | 1.63<sup>d</sup> | 2.59 | 43 |
| July 31, 2019 | **12.52** | .36 | .39 | **.75** | (.37) |  | **(.37)** | **12.90** | **6.15** | **49747** | 1.61<sup>d</sup> | 2.83 | 47 |
| July 31, 2018 | **12.54** | .39 | (.02) | **.37** | (.39) |  | **(.39)** | **12.52** | **3.00** | **58811** | 1.59 | 2.94 | 39 |
| **Class R6** |  |  |  |  |  |  |  |  |  |  |  |  |  |
| January 31, 2023<sup>\*\*</sup> | **$11.76** | .22 | (.26) | **(.04)** | (.22) |  | **(.22)** | **$11.50** | **(.21)**<sup>\*</sup> | **$1815** | .36<sup>\*d</sup> | 2.01<sup>\*</sup> | 16<sup>\*</sup> |
| July 31, 2022 | **13.53** | .41 | (1.58) | **(1.17)** | (.41) | (.19) | **(.60)** | **11.76** | **(8.90)** | **1915** | .60<sup>d</sup> | 3.24 | 34 |
| July 31, 2021 | **12.73** | .44 | .80 | **1.24** | (.44) | —<sup>c</sup> | **(.44)** | **13.53** | **9.95** | **1680** | .58<sup>d</sup> | 3.34 | 25 |
| July 31, 2020 | **12.93** | .47 | (.06) | **.41** | (.48) | (.13) | **(.61)** | **12.73** | **3.21** | **1269** | .61<sup>d</sup> | 3.61 | 43 |
| July 31, 2019 | **12.54** | .48 | .41 | **.89** | (.50) |  | **(.50)** | **12.93** | **7.30** | **1121** | .59<sup>d</sup> | 3.83 | 47 |
| July 31, 2018 <sup>†</sup> | **12.46** | .10 | .08 | **.18** | (.10) |  | **(.10)** | **12.54** | **1.41**<sup>\*</sup> | **10** | .11<sup>\*</sup> | .76<sup>\*</sup> | 39 |
| **Class Y** |  |  |  |  |  |  |  |  |  |  |  |  |  |
| January 31, 2023<sup>\*\*</sup> | **$11.76** | .22 | (.27) | **(.05)** | (.22) |  | **(.22)** | **$11.49** | **(.30)**<sup>\*</sup> | **$165797** | .37<sup>\*d</sup> | 2.00<sup>\*</sup> | 16<sup>\*</sup> |
| July 31, 2022 | **13.52** | .41 | (1.57) | **(1.16)** | (.41) | (.19) | **(.60)** | **11.76** | **(8.83)** | **146016** | .62<sup>d</sup> | 3.19 | 34 |
| July 31, 2021 | **12.73** | .43 | .80 | **1.23** | (.44) | —<sup>c</sup> | **(.44)** | **13.52** | **9.84** | **189596** | .60<sup>d</sup> | 3.32 | 25 |
| July 31, 2020 | **12.92** | .47 | (.06) | **.41** | (.47) | (.13) | **(.60)** | **12.73** | **3.27** | **147762** | .63<sup>d</sup> | 3.59 | 43 |
| July 31, 2019 | **12.54** | .48 | .40 | **.88** | (.50) |  | **(.50)** | **12.92** | **7.21** | **145164** | .61<sup>d</sup> | 3.82 | 47 |
| July 31, 2018 | **12.56** | .52 | (.02) | **.50** | (.52) |  | **(.52)** | **12.54** | **4.03** | **138347** | .59 | 3.93 | 39 |

---

See notes to financial highlights at the end of this section.

The accompanying notes are an integral part of these financial statements.

40 Tax-Free High Yield Fund Tax-Free High Yield Fund 41

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**Financial highlights** *cont.*

<sup>\*</sup> Not annualized.

<sup>\*\*</sup> Unaudited.

<sup>†</sup> For the period May 22, 2018 (commencement of operations) to July 31, 2018.

<sup>a</sup> Total return assumes dividend reinvestment and does not reflect the effect of sales charges.

<sup>b</sup> Includes amounts paid through expense offset arrangements, if any (Note 2). Also excludes acquired fund fees and expenses, if any.

<sup>c</sup> Amount represents less than $0.01 per share.

<sup>d</sup> Includes interest and fee expense associated with borrowings which amounted to (for each class):

---

| | |
|:---|:---|
| | **Percentage of average net assets** |
| January 31, 2023 | 0.07% |
| July 31, 2022 | 0.03 |
| July 31, 2021 | 0.02 |
| July 31, 2020 | 0.04 |
| July 31, 2019 | 0.02 |

---

The accompanying notes are an integral part of these financial statements.

42 Tax-Free High Yield Fund

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**Notes to financial statements** 1/31/23 (Unaudited)

Within the following Notes to financial statements, references to "State Street" represent State Street Bank and Trust Company, references to "the SEC" represent the Securities and Exchange Commission, references to "Putnam Management" represent Putnam Investment Management, LLC, the fund's manager, an indirect wholly-owned subsidiary of Putnam Investments, LLC and references to "OTC", if any, represent over-the-counter. Unless otherwise noted, the "reporting period" represents the period from August 1, 2022 through January 31, 2023.

Putnam Tax-Free High Yield Fund (the fund) is a diversified series of Putnam Tax-Free Income Trust (the Trust), a Massachusetts business trust registered under the Investment Company Act of 1940, as amended, as an open-end management investment company. The goal of the fund is to seek high current income exempt from federal income tax. The fund invests mainly in bonds that pay interest that is exempt from federal income tax (but that may be subject to federal alternative minimum tax (AMT)), are a combination of below-investment-grade and investment-grade securities, and have intermediate- to long-term maturities (i.e., three years or longer). Under normal circumstances, the fund invests at least 80% of the fund's net assets in tax-exempt investments. This investment policy cannot be changed without the approval of the fund's shareholders. Such tax-exempt investments in which the fund invests are issued by or for states, territories or possessions of the United States or by their political subdivisions, agencies, authorities or other government entities, and the income from these investments is exempt from federal income tax. Putnam Management may consider, among other factors, credit, interest rate and prepayment risks, as well as general market conditions, when deciding whether to buy or sell investments.

The fund offers the following share classes. The expenses for each class of shares may differ based on the distribution and investor servicing fees of each class, which are identified in Note 2.

---

| | | | |
|:---|:---|:---|:---|
| **Share class** | **Sales charge** | **Contingent deferred sales charge** | **Conversion feature** |
|  |  | 1.00% on certain redemptions of shares |  |
| Class A | Up to 4.00% | bought with no initial sales charge |  |
|  |  |  | Converts to class A shares |
| Class B<sup>\*</sup> |  | 5.00% phased out over six years | after 8 years |
|  |  |  | Converts to class A shares |
| Class C |  | 1.00% eliminated after one year | after 8 years |
| Class R6<sup>†</sup> |  |  |  |
| Class Y<sup>†</sup> |  |  |  |

---

<sup>\*</sup> Purchases of class B shares are closed to new and existing investors except by exchange from class B shares of another Putnam fund or through dividend and/or capital gains reinvestment.

<sup>†</sup> Not available to all investors.

In the normal course of business, the fund enters into contracts that may include agreements to indemnify another party under given circumstances. The fund's maximum exposure under these arrangements is unknown as this would involve future claims that may be, but have not yet been, made against the fund. However, the fund's management team expects the risk of material loss to be remote.

The fund has entered into contractual arrangements with an investment adviser, administrator, distributor, shareholder servicing agent and custodian, who each provide services to the fund. Unless expressly stated otherwise, shareholders are not parties to, or intended beneficiaries of these contractual arrangements, and these contractual arrangements are not intended to create any shareholder right to enforce them against the service providers or to seek any remedy under them against the service providers, either directly or on behalf of the fund.

Under the fund's Amended and Restated Agreement and Declaration of Trust, any claims asserted against or on behalf of the Putnam Funds, including claims against Trustees and Officers, must be brought in state and federal courts located within the Commonwealth of Massachusetts.

**Note 1: Significant accounting policies**

The following is a summary of significant accounting policies consistently followed by the fund in the preparation of its financial statements. The preparation of financial statements is in conformity with accounting principles generally accepted in the United States of America and requires management to make estimates and assumptions that affect the reported amounts of assets and liabilities in the financial statements and the

Tax-Free High Yield Fund 43

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reported amounts of increases and decreases in net assets from operations. Actual results could differ from those estimates. Subsequent events after the Statement of assets and liabilities date through the date that the financial statements were issued have been evaluated in the preparation of the financial statements.

Investment income, realized and unrealized gains and losses and expenses of the fund are borne pro-rata based on the relative net assets of each class to the total net assets of the fund, except that each class bears expenses unique to that class (including the distribution fees applicable to such classes). Each class votes as a class only with respect to its own distribution plan or other matters on which a class vote is required by law or determined by the Trustees. If the fund were liquidated, shares of each class would receive their pro-rata share of the net assets of the fund. In addition, the Trustees declare separate dividends on each class of shares.

**Security valuation** Portfolio securities and other investments are valued using policies and procedures adopted by the Board of Trustees. The Trustees have formed a Pricing Committee to oversee the implementation of these procedures and have delegated responsibility for valuing the fund's assets in accordance with these procedures to Putnam Management. Putnam Management has established an internal Valuation Committee that is responsible for making fair value determinations, evaluating the effectiveness of the pricing policies of the fund and reporting to the Pricing Committee.

Tax-exempt bonds and notes are generally valued on the basis of valuations provided by an independent pricing service approved by the Trustees. Such services use information with respect to transactions in bonds, quotations from bond dealers, market transactions in comparable securities and various relationships between securities in determining value. These securities will generally be categorized as Level 2.

Market quotations are not considered to be readily available for certain debt obligations (including short-term investments with remaining maturities of 60 days or less) and other investments; such investments are valued on the basis of valuations furnished by an independent pricing service approved by the Trustees or dealers selected by Putnam Management. Such services or dealers determine valuations for normal institutional-size trading units of such securities using methods based on market transactions for comparable securities and various relationships, generally recognized by institutional traders, between securities (which consider such factors as security prices, yields, maturities and ratings). These securities will generally be categorized as Level 2. Securities quoted in foreign currencies, if any, are translated into U.S. dollars at the current exchange rate.

Investments in open-end investment companies (excluding exchange-traded funds), if any, which can be classified as Level 1 or Level 2 securities, are valued based on their net asset value. The net asset value of such investment companies equals the total value of their assets less their liabilities and divided by the number of their outstanding shares.

To the extent a pricing service or dealer is unable to value a security or provides a valuation that Putnam Management does not believe accurately reflects the security's fair value, the security will be valued at fair value by Putnam Management in accordance with policies and procedures approved by the Trustees. Certain investments, including certain restricted and illiquid securities and derivatives, are also valued at fair value following procedures approved by the Trustees. These valuations consider such factors as significant market or specific security events such as interest rate or credit quality changes, various relationships with other securities, discount rates, U.S. Treasury, U.S. swap and credit yields, index levels, convexity exposures, recovery rates, sales and other multiples and resale restrictions. These securities are classified as Level 2 or as Level 3 depending on the priority of the significant inputs.

To assess the continuing appropriateness of fair valuations, the Valuation Committee reviews and affirms the reasonableness of such valuations on a regular basis after considering all relevant information that is reasonably available. Such valuations and procedures are reviewed periodically by the Trustees. The fair value of securities is generally determined as the amount that the fund could reasonably expect to realize from an orderly disposition of such securities over a reasonable period of time. By its nature, a fair value price is a good faith estimate of the value of a security in a current sale and does not reflect an actual market price, which may be different by a material amount.

**Security transactions and related investment income** Security transactions are recorded on the trade date (the date the order to buy or sell is executed). Gains or losses on securities sold are determined on the identified cost basis.

Interest income, net of any applicable withholding taxes, if any, is recorded on the accrual basis. Amortization and accretion of premiums and discounts on debt securities, if any, is recorded on the accrual basis.

44 Tax-Free High Yield Fund

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**Futures contracts** The fund uses futures contracts for hedging treasury term structure risk and for yield curve positioning.

The potential risk to the fund is that the change in value of futures contracts may not correspond to the change in value of the hedged instruments. In addition, losses may arise from changes in the value of the underlying instruments, if there is an illiquid secondary market for the contracts, if interest or exchange rates move unexpectedly or if the counterparty to the contract is unable to perform. With futures, there is minimal counterparty credit risk to the fund since futures are exchange traded and the exchange's clearinghouse, as counterparty to all exchange traded futures, guarantees the futures against default. Risks may exceed amounts recognized on the Statement of assets and liabilities. When the contract is closed, the fund records a realized gain or loss equal to the difference between the value of the contract at the time it was opened and the value at the time it was closed.

Futures contracts are valued at the quoted daily settlement prices established by the exchange on which they trade. The fund and the broker agree to exchange an amount of cash equal to the daily fluctuation in the value of the futures contract. Such receipts or payments are known as "variation margin."

Futures contracts outstanding at period end, if any, are listed after the fund's portfolio.

**Total return swap contracts** The fund entered into OTC and/or centrally cleared total return swap contracts, which are arrangements to exchange a market-linked return for a periodic payment, both based on a notional principal amount, for hedging inflation, for gaining exposure to inflation and for hedging and gaining exposure to interest rate and term structure risk.

To the extent that the total return of the security, index or other financial measure underlying the transaction exceeds or falls short of the offsetting interest rate obligation, the fund will receive a payment from or make a payment to the counterparty. OTC and/or centrally cleared total return swap contracts are marked to market daily based upon quotations from an independent pricing service or market maker. Any change is recorded as an unrealized gain or loss on OTC total return swaps. Daily fluctuations in the value of centrally cleared total return swaps are settled through a central clearing agent and are recorded in variation margin on the Statement of assets and liabilities and recorded as unrealized gain or loss. Payments received or made are recorded as realized gains or losses. Certain OTC and/or centrally cleared total return swap contracts may include extended effective dates. Payments related to these swap contracts are accrued based on the terms of the contract. The fund could be exposed to credit or market risk due to unfavorable changes in the fluctuation of interest rates or in the price of the underlying security or index, the possibility that there is no liquid market for these agreements or that the counterparty may default on its obligation to perform. The fund's maximum risk of loss from counterparty risk or central clearing risk is the fair value of the contract. This risk may be mitigated for OTC total return swap contracts by having a master netting arrangement between the fund and the counterparty and for centrally cleared total return swap contracts through the daily exchange of variation margin. There is minimal counterparty risk with respect to centrally cleared total return swap contracts due to the clearinghouse guarantee fund and other resources that are available in the event of a clearing member default. Risk of loss may exceed amounts recognized on the Statement of assets and liabilities.

OTC and/or centrally cleared total return swap contracts outstanding, including their respective notional amounts at period end, if any, are listed after the fund's portfolio.

**Master agreements** The fund is a party to ISDA (International Swaps and Derivatives Association, Inc.) Master Agreements (Master Agreements) with certain counterparties that govern OTC derivative and foreign exchange contracts entered into from time to time. The Master Agreements may contain provisions regarding, among other things, the parties' general obligations, representations, agreements, collateral requirements, events of default and early termination. With respect to certain counterparties, in accordance with the terms of the Master Agreements, collateral pledged to the fund is held in a segregated account by the fund's custodian and, with respect to those amounts which can be sold or repledged, is presented in the fund's portfolio.

Collateral pledged by the fund is segregated by the fund's custodian and identified in the fund's portfolio. Collateral can be in the form of cash or debt securities issued by the U.S. Government or related agencies or other securities as agreed to by the fund and the applicable counterparty. Collateral requirements are determined based on the fund's net position with each counterparty.

Termination events applicable to the fund may occur upon a decline in the fund's net assets below a specified threshold over a certain period of time. Termination events applicable to counterparties may occur upon a decline in the counterparty's long-term and short-term credit ratings below a specified level. In each case, upon occurrence, the other party may elect to terminate early and cause settlement of all derivative and foreign exchange contracts outstanding, including the payment of any losses and costs resulting from such early

Tax-Free High Yield Fund 45

------

termination, as reasonably determined by the terminating party. Any decision by one or more of the fund's counterparties to elect early termination could impact the fund's future derivative activity.

At the close of the reporting period, the fund did not have a net liability position on open derivative contracts subject to the Master Agreements.

**Tender option bond transactions** The fund may participate in transactions whereby a fixed-rate bond is transferred to a tender option bond trust (TOB trust) sponsored by a broker. The TOB trust funds the purchase of the fixed rate bonds by issuing floating-rate bonds to third parties and allowing the fund to retain the residual interest in the TOB trust's assets and cash flows, which are in the form of inverse floating rate bonds. The inverse floating rate bonds held by the fund give the fund the right to (1) cause the holders of the floating rate bonds to tender their notes at par, and (2) to have the fixed-rate bond held by the TOB trust transferred to the fund, causing the TOB trust to collapse. The fund accounts for the transfer of the fixed-rate bond to the TOB trust as a secured borrowing by including the fixed-rate bond in the fund's portfolio and including the floating rate bond as a liability in the Statement of assets and liabilities. At the close of the reporting period, the fund's investments with a value of $59,595,606 were held by the TOB trust and served as collateral for $36,878,184 in floating-rate bonds outstanding. For the reporting period ended, the fund incurred interest expense of $381,568 for these investments based on an average interest rate of 2.26%.

**Interfund lending** The fund, along with other Putnam funds, may participate in an interfund lending program pursuant to an exemptive order issued by the SEC. This program allows the fund to borrow from other Putnam funds that permit such transactions. Interfund lending transactions are subject to each fund's investment policies and borrowing and lending limits. Interest earned or paid on the interfund lending transaction will be based on the average of certain current market rates. During the reporting period, the fund did not utilize the program.

**Lines of credit** The fund participates, along with other Putnam funds, in a $100 million ($317.5 million prior to October 14, 2022) unsecured committed line of credit and a $235.5 million unsecured uncommitted line of credit, both provided by State Street. Borrowings may be made for temporary or emergency purposes, including the funding of shareholder redemption requests and trade settlements. Interest is charged to the fund based on the fund's borrowing at a rate equal to 1.25% plus the higher of (1) the Federal Funds rate and (2) the Overnight Bank Funding Rate for the committed line of credit and 1.30% plus the higher of (1) the Federal Funds rate and (2) the Overnight Bank Funding Rate for the uncommitted line of credit. A closing fee equal to 0.04% of the committed line of credit and 0.04% of the uncommitted line of credit has been paid by the participating funds. In addition, a commitment fee of 0.21% per annum on any unutilized portion of the committed line of credit is allocated to the participating funds based on their relative net assets and paid quarterly. During the reporting period, the fund had no borrowings against these arrangements.

**Federal taxes** It is the policy of the fund to distribute all of its income within the prescribed time period and otherwise comply with the provisions of the Internal Revenue Code of 1986, as amended (the Code), applicable to regulated investment companies. It is also the intention of the fund to distribute an amount sufficient to avoid imposition of any excise tax under Section 4982 of the Code.

The fund is subject to the provisions of Accounting Standards Codification 740 *Income Taxes* (ASC 740). ASC 740 sets forth a minimum threshold for financial statement recognition of the benefit of a tax position taken or expected to be taken in a tax return. The fund did not have a liability to record for any unrecognized tax benefits in the accompanying financial statements. No provision has been made for federal taxes on income, capital gains or unrealized appreciation on securities held nor for excise tax on income and capital gains. Each of the fund's federal tax returns for the prior three fiscal years remains subject to examination by the Internal Revenue Service.

Pursuant to federal income tax regulations applicable to regulated investment companies, the fund has elected to defer certain capital losses of $5,251,840 recognized during the period between November 1, 2021 and July 31, 2022 to its fiscal year ending July 21, 2023.

Tax cost of investments includes adjustments to net unrealized appreciation (depreciation) which may not necessarily be final tax cost basis adjustments, but closely approximate the tax basis unrealized gains and losses that may be realized and distributed to shareholders. The aggregate identified cost on a tax basis is $778,234,323, resulting in gross unrealized appreciation and depreciation of $16,881,505 and $55,038,950, respectively, or net unrealized depreciation of $38,157,445.

**Distributions to shareholders** Income dividends are recorded daily by the fund and are paid monthly. Distributions from capital gains, if any, are recorded on the ex-dividend date and paid at least annually. The amount and character of income and gains to be distributed are determined in accordance with income tax regulations, which may differ from generally accepted accounting principles. Dividend sources are estimated at the time

46 Tax-Free High Yield Fund

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of declaration. Actual results may vary. Any non-taxable return of capital cannot be determined until final tax calculations are completed after the end of the fund's fiscal year. Reclassifications are made to the fund's capital accounts to reflect income and gains available for distribution (or available capital loss carryovers) under income tax regulations.

**Expenses of the Trust** Expenses directly charged or attributable to any fund will be paid from the assets of that fund. Generally, expenses of the Trust will be allocated among and charged to the assets of each fund on a basis that the Trustees deem fair and equitable, which may be based on the relative assets of each fund or the nature of the services performed and relative applicability to each fund.

**Note 2: Management fee, administrative services and other transactions**

The fund pays Putnam Management a management fee (based on the fund's average net assets and computed and paid monthly) at annual rates that may vary based on the average of the aggregate net assets of all open-end mutual funds sponsored by Putnam Management (excluding net assets of funds that are invested in, or that are invested in by, other Putnam funds to the extent necessary to avoid "double counting" of those assets). Such annual rates may vary as follows:

---

| | | | |
|:---|:---|:---|:---|
| 0.630% | of the first $5 billion, | 0.430% | of the next $50 billion, |
| 0.580% | of the next $5 billion, | 0.410% | of the next $50 billion, |
| 0.530% | of the next $10 billion, | 0.400% | of the next $100 billion and |
| 0.480% | of the next $10 billion, | 0.395% | of any excess thereafter. |

---

For the reporting period, the management fee represented an effective rate (excluding the impact from any expense waivers in effect) of 0.237% of the fund's average net assets.

Putnam Management has contractually agreed, through November 30, 2023, to waive fees and/or reimburse the fund's expenses to the extent necessary to limit the cumulative expenses of the fund, exclusive of brokerage, interest, taxes, investment-related expenses, extraordinary expenses, acquired fund fees and expenses and payments under the fund's investor servicing contract, investment management contract and distribution plans, on a fiscal year-to-date basis to an annual rate of 0.20% of the fund's average net assets over such fiscal year-to-date period. During the reporting period, the fund's expenses were not reduced as a result of this limit.

Putnam Investments Limited (PIL), an affiliate of Putnam Management, is authorized by the Trustees to manage a separate portion of the assets of the fund as determined by Putnam Management from time to time. PIL did not manage any portion of the assets of the fund during the reporting period. If Putnam Management were to engage the services of PIL, Putnam Management would pay a quarterly sub-management fee to PIL for its services at an annual rate of 0.20% of the average net assets of the portion of the fund managed by PIL.

The fund reimburses Putnam Management an allocated amount for the compensation and related expenses of certain officers of the fund and their staff who provide administrative services to the fund. The aggregate amount of all such reimbursements is determined annually by the Trustees.

Custodial functions for the fund's assets are provided by State Street. Custody fees are based on the fund's asset level, the number of its security holdings and transaction volumes.

Putnam Investor Services, Inc., an affiliate of Putnam Management, provides investor servicing agent functions to the fund. Putnam Investor Services, Inc. received fees for investor servicing for class A, class B, class C and class Y shares that included (1) a per account fee for each direct and underlying non-defined contribution account (retail account) of the fund; (2) a specified rate of the fund's assets attributable to defined contribution plan accounts; and (3) a specified rate based on the average net assets in retail accounts. Putnam Investor Services, Inc. has agreed that the aggregate investor servicing fees for each fund's retail and defined contribution accounts for these share classes will not exceed an annual rate of 0.25% of the fund's average assets attributable to such accounts.

Class R6 shares paid a monthly fee based on the average net assets of class R6 shares at an annual rate of 0.05%.

Tax-Free High Yield Fund 47

------

During the reporting period, the expenses for each class of shares related to investor servicing fees were as follows:

---

| | | | |
|:---|:---|:---|:---|
| Class A | $197637 | Class R6 | 456 |
| Class B | 422 | Class Y | 57632 |
| Class C | 6145 | **Total** | **$262292** |

---

The fund has entered into expense offset arrangements with Putnam Investor Services, Inc. and State Street whereby Putnam Investor Services, Inc.'s and State Street's fees are reduced by credits allowed on cash balances. For the reporting period, the fund's expenses were reduced by $2,167 under the expense offset arrangements.

Each Independent Trustee of the fund receives an annual Trustee fee, of which $608 as a quarterly retainer, has been allocated to the fund, and an additional fee for each Trustees meeting attended. Trustees also are reimbursed for expenses they incur relating to their services as Trustees.

The fund has adopted a Trustee Fee Deferral Plan (the Deferral Plan) which allows the Trustees to defer the receipt of all or a portion of Trustees fees payable on or after July 1, 1995. The deferred fees remain invested in certain Putnam funds until distribution in accordance with the Deferral Plan.

The fund has adopted an unfunded noncontributory defined benefit pension plan (the Pension Plan) covering all Trustees of the fund who have served as a Trustee for at least five years and were first elected prior to 2004. Benefits under the Pension Plan are equal to 50% of the Trustee's average annual attendance and retainer fees for the three years ended December 31, 2005. The retirement benefit is payable during a Trustee's lifetime, beginning the year following retirement, for the number of years of service through December 31, 2006. Pension expense for the fund is included in Trustee compensation and expenses in the Statement of operations. Accrued pension liability is included in Payable for Trustee compensation and expenses in the Statement of assets and liabilities. The Trustees have terminated the Pension Plan with respect to any Trustee first elected after 2003.

The fund has adopted distribution plans (the Plans) with respect to the following share classes pursuant to Rule 12b–1 under the Investment Company Act of 1940. The purpose of the Plans is to compensate Putnam Retail Management Limited Partnership, an indirect wholly-owned subsidiary of Putnam Investments, LLC, for services provided and expenses incurred in distributing shares of the fund. The Plans provide payments by the fund to Putnam Retail Management Limited Partnership at an annual rate of up to the following amounts (Maximum %) of the average net assets attributable to each class. The Trustees have approved payment by the fund at the following annual rate (Approved %) of the average net assets attributable to each class. During the reporting period, the class-specific expenses related to distribution fees were as follows:

---

| | | | |
|:---|:---|:---|:---|
|  | **Maximum %** | **Approved %** | **Amount** |
| Class A | 0.35% | 0.25% | $656868 |
| Class B | 1.00% | 0.85% | 4767 |
| Class C | 1.00% | 1.00% | 81704 |
| **Total** |  |  | **$743339** |

---

For the reporting period, Putnam Retail Management Limited Partnership, acting as underwriter, received net commissions of $4,998 from the sale of class A shares and received $0 and $40 in contingent deferred sales charges from redemptions of class B and class C shares, respectively.

A deferred sales charge of up to 1.00% is assessed on certain redemptions of class A shares. For the reporting period, Putnam Retail Management Limited Partnership, acting as underwriter, received $0 on class A redemptions.

**Note 3: Purchases and sales of securities**

During the reporting period, the cost of purchases and the proceeds from sales, excluding short-term investments, were as follows:

---

| | | |
|:---|:---|:---|
|  | **Cost of purchases** | **Proceeds from sales** |
| Investments in securities (Long-term) | $108856181 | $116165562 |
| U.S. government securities (Long-term) |  |  |
| **Total** | **$108856181** | **$116165562** |

---

48 Tax-Free High Yield Fund

------

The fund may purchase or sell investments from or to other Putnam funds in the ordinary course of business, which can reduce the fund's transaction costs, at prices determined in accordance with SEC requirements and policies approved by the Trustees. During the reporting period, purchases or sales of long-term securities from or to other Putnam funds, if any, did not represent more than 5% of the fund's total cost of purchases and/or total proceeds from sales.

**Note 4: Capital shares**

At the close of the reporting period, there were an unlimited number of shares of beneficial interest authorized. Transactions, including, if applicable, direct exchanges pursuant to share conversions, in capital shares were as follows:

---

| | | | | |
|:---|:---|:---|:---|:---|
|  | **SIX MONTHS ENDED 1/31/23** | **SIX MONTHS ENDED 1/31/23** | **YEAR ENDED 7/31/22** | **YEAR ENDED 7/31/22** |
| **Class A** | **Shares** | **Amount** | **Shares** | **Amount** |
| Shares sold | 3239498 | $36239040 | 4331554 | $53519675 |
| Shares issued in connection with |  |  |  |  |
| reinvestment of distributions | 779130 | 8557707 | 1989555 | 25097193 |
|  | 4018628 | 44796747 | 6321109 | 78616868 |
| Shares repurchased | (6713334) | (74049897) | (8676040) | (106113326) |
| **Net decrease** | **(2694706)** | **$(29253150)** | **(2354931)** | **$(27496458)** |
|  | **SIX MONTHS ENDED 1/31/23** | **SIX MONTHS ENDED 1/31/23** | **YEAR ENDED 7/31/22** | **YEAR ENDED 7/31/22** |
| **Class B** | **Shares** | **Amount** | **Shares** | **Amount** |
| Shares sold | 144 | $1591 | 621 | $7910 |
| Shares issued in connection with |  |  |  |  |
| reinvestment of distributions | 1251 | 13770 | 5082 | 64667 |
|  | 1395 | 15361 | 5703 | 72577 |
| Shares repurchased | (47574) | (515898) | (76063) | (947976) |
| **Net decrease** | **(46179)** | **$(500537)** | **(70360)** | **$(875399)** |
|  | **SIX MONTHS ENDED 1/31/23** | **SIX MONTHS ENDED 1/31/23** | **YEAR ENDED 7/31/22** | **YEAR ENDED 7/31/22** |
| **Class C** | **Shares** | **Amount** | **Shares** | **Amount** |
| Shares sold | 98195 | $1100814 | 328281 | $4245301 |
| Shares issued in connection with |  |  |  |  |
| reinvestment of distributions | 21006 | 231336 | 61610 | 782025 |
|  | 119201 | 1332150 | 389891 | 5027326 |
| Shares repurchased | (303982) | (3385565) | (632736) | (7920447) |
| **Net decrease** | **(184781)** | **$(2053415)** | **(242845)** | **$(2893121)** |
|  | **SIX MONTHS ENDED 1/31/23** | **SIX MONTHS ENDED 1/31/23** | **YEAR ENDED 7/31/22** | **YEAR ENDED 7/31/22** |
| **Class R6** | **Shares** | **Amount** | **Shares** | **Amount** |
| Shares sold | 35775 | $404630 | 68968 | $834539 |
| Shares issued in connection with |  |  |  |  |
| reinvestment of distributions | 3321 | 36647 | 6701 | 84488 |
|  | 39096 | 441277 | 75669 | 919027 |
| Shares repurchased | (44058) | (483731) | (37098) | (447695) |
| **Net increase (decrease)** | **(4962)** | **$(42454)** | **38571** | **$471332** |

---

Tax-Free High Yield Fund 49

------

---

| | | | | |
|:---|:---|:---|:---|:---|
|  | **SIX MONTHS ENDED 1/31/23** | **SIX MONTHS ENDED 1/31/23** | **YEAR ENDED 7/31/22** | **YEAR ENDED 7/31/22** |
| **Class Y** | **Shares** | **Amount** | **Shares** | **Amount** |
| Shares sold | 5968847 | $66781300 | 6038701 | $75161153 |
| Shares issued in connection with |  |  |  |  |
| reinvestment of distributions | 258928 | 2857320 | 608919 | 7719694 |
|  | 6227775 | 69638620 | 6647620 | 82880847 |
| Shares repurchased | (4220320) | (46690571) | (8247659) | (100240213) |
| **Net increase (decrease)** | **2007455** | **$22948049** | **(1600039)** | **$(17359366)** |

---

**Note 5: Affiliated transactions**

Transactions during the reporting period with any company which is under common ownership or control were as follows:

---

| | | | | | |
|:---|:---|:---|:---|:---|:---|
|  |  |  |  |  | **Shares** |
|  |  |  |  |  | **outstanding** |
|  |  |  |  |  | **and fair** |
|  | **Fair value as** | **Purchase** | **Sale** | **Investment** | **value as** |
| **Name of affiliate** | **of 7/31/22** | **cost** | **proceeds** | **income** | **of 1/31/23** |
| **Short-term investments** |  |  |  |  |  |
| Putnam Short Term |  |  |  |  |  |
| Investment Fund<sup>\*</sup> | $14473590 | $158479074 | $159710516 | $228026 | $13242148 |
| **Total Short-term** |  |  |  |  |  |
| **investments** | **$14473590** | **$158479074** | **$159710516** | **$228026** | **$13242148** |

---

<sup>\*</sup> Management fees charged to Putnam Short Term Investment Fund have been waived by Putnam Management. There were no realized or unrealized gains or losses during the period.

**Note 6: Market, credit and other risks**

In the normal course of business, the fund trades financial instruments and enters into financial transactions where risk of potential loss exists due to changes in the market (market risk) or failure of the contracting party to the transaction to perform (credit risk). The fund may be exposed to additional credit risk that an institution or other entity with which the fund has unsettled or open transactions will default.

On July 27, 2017, the United Kingdom's Financial Conduct Authority ("FCA"), which regulates LIBOR, announced its intention to cease compelling banks to provide the quotations needed to sustain LIBOR after 2021. ICE Benchmark Administration, the administrator of LIBOR, ceased publication of most LIBOR settings on a representative basis at the end of 2021 and is expected to cease publication of a majority of U.S. dollar LIBOR settings on a representative basis after June 30, 2023. In addition, global regulators have announced that, with limited exceptions, no new LIBOR-based contracts should be entered into after 2021. LIBOR has historically been a common benchmark interest rate index used to make adjustments to variable-rate loans. It is used throughout global banking and financial industries to determine interest rates for a variety of financial instruments and borrowing arrangements. Actions by regulators have resulted in the establishment of alternative reference rates to LIBOR in most major currencies. Various financial industry groups have been planning for the transition away from LIBOR, but there are obstacles to converting certain longer-term securities and transactions to new reference rates. Markets are developing slowly and questions around liquidity in these rates and how to appropriately adjust these rates to mitigate any economic value transfer at the time of transition remain a significant concern. Neither the effect of the transition process nor its ultimate success can yet be known. The transition process might lead to increased volatility and illiquidity in markets that rely on LIBOR to determine interest rates. It could also lead to a reduction in the value of some LIBOR-based investments and reduce the effectiveness of related transactions, such as hedges. While some LIBOR-based instruments may contemplate a scenario where LIBOR is no longer available by providing for an alternative rate-setting methodology, not all may have such provisions and there may be significant uncertainty regarding the effectiveness of any such alternative methodologies. Since the usefulness of LIBOR as a benchmark could deteriorate during the transition period, these effects could occur at any time.

50 Tax-Free High Yield Fund

------

The Covid–19 pandemic and efforts to contain its spread have resulted in, among other effects, significant market volatility, exchange trading suspensions and closures, declines in global financial markets, higher default rates, significant changes in fiscal and monetary policies, and economic downturns and recessions. The effects of the Covid–19 pandemic have negatively affected, and may continue to negatively affect, the global economy, the economies of the United States and other individual countries, the financial performance of individual issuers, sectors, industries, asset classes, and markets, and the value, volatility, and liquidity of particular securities and other assets. The effects of the Covid–19 pandemic also are likely to exacerbate other risks that apply to the fund, which could negatively impact the fund's performance and lead to losses on your investment in the fund. The duration of the Covid–19 pandemic and its effects cannot be determined with certainty.

**Note 7: Summary of derivative activity**

The volume of activity for the reporting period for any derivative type that was held during the period is listed below and was based on an average of the holdings at the end of each fiscal quarter:

---

| | |
|:---|:---|
| Futures contracts (number of contracts) | 300 |
| OTC total return swap contracts (notional) | $1300000 |

---

The following is a summary of the fair value of derivative instruments as of the close of the reporting period:

---

| | | | | |
|:---|:---|:---|:---|:---|
| **Fair value of derivative instruments as of the close of the reporting period** | **Fair value of derivative instruments as of the close of the reporting period** | **Fair value of derivative instruments as of the close of the reporting period** | **Fair value of derivative instruments as of the close of the reporting period** |  |
| | **ASSET DERIVATIVES** | **ASSET DERIVATIVES** | **LIABILITY DERIVATIVES** | **LIABILITY DERIVATIVES** |
| **Derivatives not**<br>**accounted for as**<br>**hedging instruments**<br>**under ASC 815** | <br>**Statement of**<br>**assets and**<br>**liabilities location** | <br>**Fair value** | <br>**Statement of**<br>**assets and**<br>**liabilities location** | <br>**Fair value** |
| Interest rate contracts | Receivables | $2140<sup>\*</sup> | Payables | $721006<sup>\*</sup> |
| **Total** |  | **$2140** |  | **$721006** |

---

<sup>\*</sup>Includes cumulative appreciation/depreciation of futures contracts as reported in the fund's portfolio. Only current day's variation margin is reported within the Statement of assets and liabilities.

The following is a summary of realized and change in unrealized gains or losses of derivative instruments in the Statement of operations for the reporting period (Note 1):

---

| | | | |
|:---|:---|:---|:---|
| **Amount of realized gain or (loss) on derivatives recognized in net gain or (loss) on investments** | **Amount of realized gain or (loss) on derivatives recognized in net gain or (loss) on investments** | **Amount of realized gain or (loss) on derivatives recognized in net gain or (loss) on investments** | **Amount of realized gain or (loss) on derivatives recognized in net gain or (loss) on investments** |
| **Derivatives not accounted for as hedging** |  |  |  |
| **instruments under ASC 815** | **Futures** | **Swaps** | **Total** |
| Interest rate contracts | $2067919 | $724950 | $2792869 |
| **Total** | **$2067919** | **$724950** | **$2792869** |

---

---

| | | | |
|:---|:---|:---|:---|
| **Change in unrealized appreciation or (depreciation) on derivatives recognized in net gain or (loss)** | **Change in unrealized appreciation or (depreciation) on derivatives recognized in net gain or (loss)** | **Change in unrealized appreciation or (depreciation) on derivatives recognized in net gain or (loss)** | **Change in unrealized appreciation or (depreciation) on derivatives recognized in net gain or (loss)** |
| **on investments** |  |  |  |
| **Derivatives not accounted for as hedging** |  |  |  |
| **instruments under ASC 815** | **Futures** | **Swaps** | **Total** |
| Interest rate contracts | $(610502) | $(833156) | $(1443658) |
| **Total** | **$(610502)** | **$(833156)** | **$(1443658)** |

---

Tax-Free High Yield Fund 51

------

**Note 8: Offsetting of financial and derivative assets and liabilities**

The following table summarizes any derivatives, repurchase agreements and reverse repurchase agreements, at the end of the reporting period, that are subject to an enforceable master netting agreement or similar agreement. For securities lending transactions or borrowing transactions associated with securities sold short, if any, see Note 1. For financial reporting purposes, the fund does not offset financial assets and financial liabilities that are subject to the master netting agreements in the Statement of assets and liabilities.

---

| | | |
|:---|:---|:---|
| <br>**Assets:** | **JPMorgan Securities LLC** | **Total** |
| Futures contracts<sup>§</sup> | $— | $— |
| **Total Assets** | **$—** | **$—** |
| **Liabilities:** |  |  |
| Futures contracts<sup>§</sup> | 108784 | 108784 |
| **Total Liabilities** | **$108784** | **$108784** |
| **Total Financial and Derivative Net Assets** | **$(108784)** | **$(108784)** |
| Total collateral received (pledged)<sup>†##</sup> | $— |  |
| Net amount | $(108784) |  |
| *Controlled collateral received (including* |  |  |
| *TBA commitments)*<sup>\*\*</sup> | $— | $— |
| *Uncontrolled collateral received* | $— | $— |
| *Collateral (pledged) (including TBA commitments)*<sup>\*\*</sup> | $— | $— |

---

<sup>†</sup> Additional collateral may be required from certain brokers based on individual agreements.

<sup>##</sup> Any over-collateralization of total financial and derivative net assets is not shown. Collateral may include amounts related to unsettled agreements.

<sup>§</sup> Includes current day's variation margin only as reported on the Statement of assets and liabilities, which is not collateralized. Cumulative appreciation/(depreciation) for futures contracts and centrally cleared swap contracts is represented in the tables listed after the fund's portfolio. Collateral pledged for initial margin on futures contracts, which is not included in the table above, amounted to $1,235,521.

52 Tax-Free High Yield Fund

------

**Fund information**

Founded over 85 years ago, Putnam Investments was built around the concept that a balance between risk and reward is the hallmark of a well-rounded financial program. We manage funds across income, value, blend, growth, sustainable, and asset allocation categories.

---

| | | |
|:---|:---|:---|
| **Investment Manager** | **Trustees** | Richard T. Kircher |
| Putnam Investment | Kenneth R. Leibler, *Chair* | *Vice President and* |
| Management, LLC | Barbara M. Baumann, *Vice Chair* | *BSA Compliance Officer* |
| 100 Federal Street | Liaquat Ahamed |  |
| Boston, MA 02110 | Katinka Domotorffy | Martin Lemaire |
|  | Catharine Bond Hill | *Vice President and* |
| **Investment Sub-Advisor** | Jennifer Williams Murphy | *Derivatives Risk Manager* |
| Putnam Investments Limited | Marie Pillai |  |
| 16 St James's Street | George Putnam III | Susan G. Malloy |
| London, England SW1A 1ER | Robert L. Reynolds | *Vice President and* |
|  | Manoj P. Singh | *Assistant Treasurer* |
| **Marketing Services** | Mona K. Sutphen |  |
| Putnam Retail Management |  | Alan G. McCormack |
| Limited Partnership | **Officers** | *Vice President and* |
| 100 Federal Street | Robert L. Reynolds | *Derivatives Risk Manager* |
| Boston, MA 02110 | *President* |  |
|  |  | Denere P. Poulack |
| **Custodian** | James F. Clark | *Assistant Vice President,* |
| State Street Bank | *Vice President, Chief Compliance* | *Assistant Clerk, and* |
| and Trust Company | *Officer, and Chief Risk Officer* | *Assistant Treasurer* |
| **Legal Counsel** | Nancy E. Florek | Janet C. Smith |
| Ropes & Gray LLP | *Vice President, Assistant Clerk,* | *Vice President,* |
|  | *and Assistant Treasurer* | *Principal Financial Officer,* |
|  |  | *Principal Accounting Officer,* |
|  | Michael J. Higgins | *and Assistant Treasurer* |
|  | *Vice President, Treasurer,* |  |
|  | *and Clerk* | Stephen J. Tate |
|  |  | *Vice President and* |
|  | Jonathan S. Horwitz | *Chief Legal Officer* |
|  | *Executive Vice President,* |  |
|  | *Principal Executive Officer,* | Mark C. Trenchard |
|  | *and Compliance Liaison* | *Vice President* |

---

*This report is for the information of shareholders of Putnam Tax-Free High Yield Fund. It may also be used as sales literature when preceded or accompanied by the current prospectus, the most recent copy of Putnam's Quarterly Performance Summary, and Putnam's Quarterly Ranking Summary. For more recent performance, please visit putnam.com. Investors should carefully consider the investment objectives, risks, charges, and expenses of a fund, which are described in its prospectus. For this and other information or to request a prospectus or summary prospectus, call 1-800-225-1581 toll free. Please read the prospectus carefully before investing. The fund's Statement of Additional Information contains additional information about the fund's Trustees and is available without charge upon request by calling 1-800-225-1581.*

------

![](taxfreehighyieldx56x1.jpg) <br>

<u>Item 2. Code of Ethics:</u>

Not applicable

<u>Item 3. Audit Committee Financial Expert:</u>

Not applicable

<u>Item 4. Principal Accountant Fees and Services:</u>

Not applicable

<u>Item 5. Audit Committee of Listed Registrants</u>

Not applicable

<u>Item 6. Schedule of Investments:</u>

The registrant's schedule of investments in unaffiliated issuers is included in the report to shareholders in Item 1 above.

<u>Item 7. Disclosure of Proxy Voting Policies and Procedures For Closed-End Management Investment Companies:</u>

Not applicable

<u>Item 8. Portfolio Managers of Closed-End Investment Companies</u>

Not Applicable

<u>Item 9. Purchases of Equity Securities by Closed-End Management Investment Companies and Affiliated Purchasers:</u>

Not applicable

<u>Item 10. Submission of Matters to a Vote of Security Holders:</u>

Not applicable

<u>Item 11. Controls and Procedures:</u>

(a) The registrant's principal executive officer and principal financial officer have concluded, based on their evaluation of the effectiveness of the design and operation of the registrant's disclosure controls and procedures as of a date within 90 days of the filing date of this report, that the design and operation of such procedures are generally effective to provide reasonable assurance that information required to be disclosed by the registrant in this report is recorded, processed, summarized and reported within the time periods specified in the Commission's rules and forms.

(b) Changes in internal control over financial reporting: Not applicable

<u>Item 12. Disclosures of Securities Lending Activities for Closed-End Investment Companies:</u>

Not Applicable

<u>Item 13. Exhibits:</u>

(a)(1) Not applicable

[(a)(2) Separate certifications for the principal executive officer and principal financial officer of the registrant as required by Rule 30a-2(a) under the Investment Company Act of 1940, as amended, are filed herewith.](b_036certifications.htm)

[(b) The certifications required by Rule 30a-2(b) under the Investment Company Act of 1940, as amended, are filed herewith.](c_036noscertification.htm)

<u>SIGNATURES</u>

Pursuant to the requirements of the Securities Exchange Act of 1934 and the Investment Company Act of 1940, the registrant has duly caused this report to be signed on its behalf by the undersigned, thereunto duly authorized.

<u>Putnam Tax Free Income Trust</u>

By (Signature and Title):

<u>/s/ Janet C. Smith</u><br>Janet C. Smith<br>Principal Accounting Officer<br>

Date: March 29, 2023

Pursuant to the requirements of the Securities Exchange Act of 1934 and the Investment Company Act of 1940, this report has been signed below by the following persons on behalf of the registrant and in the capacities and on the dates indicated.

By (Signature and Title):

<u>/s/ Jonathan S. Horwitz</u><br>Jonathan S. Horwitz<br>Principal Executive Officer<br>

Date: March 29, 2023

By (Signature and Title):

<u>/s/ Janet C. Smith</u><br>Janet C. Smith<br>Principal Financial Officer<br>

Date: March 29, 2023

## Ex-99.Cert

---

| |
|:---|
| <u>Certifications<br></u>  |
| I, Jonathan S. Horwitz, the Principal Executive Officer of the funds listed on Attachment A, certify that: |
| <br>1. I have reviewed each report on Form N-CSR of the funds listed on Attachment A: |
| <br>2. Based on my knowledge, each report does not contain any untrue statements of a material fact or omit to state a material fact necessary to make the statements made, in light of the circumstances under which such statements were made, not misleading with respect to the period covered by each report; |
| <br>3. Based on my knowledge, the financial statements, and other financial information included in each report, fairly present in all material respects the financial condition, results of operations, changes in net assets, and cash flows (if the financial statements are required to include a statement of cash flows) of the registrant as of, and for, the periods presented in each report; |
| <br>4. The registrant's other certifying officer and I are responsible for establishing and maintaining disclosure controls and procedures (as defined in Rule 30a-3(c) under the Investment Company Act of 1940) and internal control over financial reporting (as defined in Rule 30a-3(d) under the Investment Company Act of 1940) for the registrant and have: |
| <br>a) designed such disclosure controls and procedures, or caused such disclosure controls and procedures to be designed under our supervision, to ensure that material information relating to the registrant, including its consolidated subsidiaries, is made known to us by others within those entities, particularly during the period in which each report is being prepared; |
| <br>b) designed such internal control over financial reporting, or caused such internal control over financial reporting to be designed under our supervision, to provide reasonable assurance regarding the reliability of financial reporting and the preparation of financial statements for external purposes in accordance with generally accepted accounting principles; |
| <br>c) evaluated the effectiveness of the registrant's disclosure controls and procedures and presented in this report our conclusions about the effectiveness of the disclosure controls and procedures, as of a date within 90 days prior to the filing date of each report based on such evaluation; and |
| <br>d) disclosed in this report any change in the registrant's internal control over financial reporting that occurred during the period covered by the registrant's report that has materially affected, or is reasonably likely to materially affect, the registrant's internal control over financial reporting; and |
| <br>5. The registrant's other certifying officer and I have disclosed to each registrant's auditors and the audit committee of each registrant's board of directors (or persons performing the equivalent functions): |
| <br>a) all significant deficiencies and material weaknesses in the design or operation of internal control over financial reporting which are reasonably likely to adversely affect each registrant's ability to record, process, summarize, and report financial information; and |
| <br>b) any fraud, whether or not material, that involves management or other employees who have a significant role in each registrant's internal control over financial reporting. |
| <br>Date: March 29, 2023 |
| <br>/s/ Jonathan S. Horwitz |
| _______________________ |
| Jonathan S. Horwitz |
| Principal Executive Officer |
| <br><u><br><u>Certifications<br></u></u>  |
| I, Janet C. Smith, the Principal Financial Officer of the funds listed on Attachment A, certify that: |
| <br>1. I have reviewed each report on Form N-CSR of the funds listed on Attachment A: |
| <br>2. Based on my knowledge, each report does not contain any untrue statements of a material fact or omit to state a material fact necessary to make the statements made, in light of the circumstances under which such statements were made, not misleading with respect to the period covered by each report; |
| <br>3. Based on my knowledge, the financial statements, and other financial information included in each report, fairly present in all material respects the financial condition, results of operations, changes in net assets, and cash flows (if the financial statements are required to include a statement of cash flows) of the registrant as of, and for, the periods presented in each report; |
| <br>4. The registrant's other certifying officer and I are responsible for establishing and maintaining disclosure controls and procedures (as defined in Rule 30a-3(c) under the Investment Company Act of 1940) and internal control over financial reporting (as defined in Rule 30a-3(d) under the Investment Company Act of 1940) for the registrant and have: |
| <br>a) designed such disclosure controls and procedures, or caused such disclosure controls and procedures to be designed under our supervision, to ensure that material information relating to the registrant, including its consolidated subsidiaries, is made known to us by others within those entities, particularly during the period in which each report is being prepared; |
| <br>b) designed such internal control over financial reporting, or caused such internal control over financial reporting to be designed under our supervision, to provide reasonable assurance regarding the reliability of financial reporting and the preparation of financial statements for external purposes in accordance with generally accepted accounting principles; |
| <br>c) evaluated the effectiveness of the registrant's disclosure controls and procedures and presented in this report our conclusions about the effectiveness of the disclosure controls and procedures, as of a date within 90 days prior to the filing date of each report based on such evaluation; and |
| <br>d) disclosed in this report any change in the registrant's internal control over financial reporting that occurred during the period covered by the registrant's report that has materially affected, or is reasonably likely to materially affect, the registrant's internal control over financial reporting; and |
| <br>5. The registrant's other certifying officer and I have disclosed to each registrant's auditors and the audit committee of each registrant's board of directors (or persons performing the equivalent functions): |
| <br>a) all significant deficiencies and material weaknesses in the design or operation of internal control over financial reporting which are reasonably likely to adversely affect each registrant's ability to record, process, summarize, and report financial information; and |
| <br>b) any fraud, whether or not material, that involves management or other employees who have a significant role in each registrant's internal control over financial reporting. |
| <br>Date: March 29, 2023 |
| <br>/s/ Janet C. Smith |
| _______________________ |
| Janet C. Smith |
| Principal Financial Officer |
| <br>**Attachment A** |
| <br>Period (s) ended January 31, 2023<br>|
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;George Putnam Balanced Fund |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Putnam Growth Opportunities Fund |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Putnam Premier Income Trust |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Putnam Research Fund |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Putnam Ultra Short Duration Income Fund |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Putnam Short Term Investment Fund |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Putnam Strategic Intermediate Municipal Fund |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Putnam Tax-Free High Yield Fund |
| <br> Putnam Sustainable Retirement 2065 Fund |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Putnam Sustainable Retirement 2060 Fund |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Putnam Sustainable Retirement 2055 Fund |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Putnam Sustainable Retirement 2050 Fund |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Putnam Sustainable Retirement 2045 Fund |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Putnam Sustainable Retirement 2040 Fund |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Putnam Sustainable Retirement 2035 Fund |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Putnam Sustainable Retirement 2030 Fund |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Putnam Sustainable Retirement 2025 Fund |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Putnam Sustainable Retirement Maturity Fund |

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## Exhibit 99.906

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| |
|:---|
| <u>Section 906 Certifications<br></u>  |
| I, Jonathan S. Horwitz, the Principal Executive Officer of the Funds listed on Attachment A, certify that, to my knowledge: |
| <br>1. The form N-CSR of the Funds listed on Attachment A for the period ended January 31, 2023 fully complies with the requirements of Section 13(a) or 15(d) of the Securities Exchange Act of 1934; and |
| <br>2. The information contained in the Form N-CSR of the Funds listed on Attachment A for the period ended January 31, 2023 fairly presents, in all material respects, the financial condition and results of operations of the Funds listed on Attachment A. |
| <br>Date: March 29, 2023 |
| <br>/s/ Jonathan S. Horwitz |
| ______________________ |
| Jonathan S. Horwitz |
| Principal Executive Officer |
| <br><u><br><u>Section 906 Certifications<br></u></u>  |
| I, Janet C. Smith, the Principal Financial Officer of the Funds listed on Attachment A, certify that, to my knowledge: |
| <br>1. The form N-CSR of the Funds listed on Attachment A for the period ended January 31, 2023 fully complies with the requirements of Section 13(a) or 15(d) of the Securities Exchange Act of 1934; and |
| <br>2. The information contained in the Form N-CSR of the Funds listed on Attachment A for the period ended January 31, 2023 fairly presents, in all material respects, the financial condition and results of operations of the Funds listed on Attachment A. |
| <br>Date: March 29, 2023 |
| <br>/s/ Janet C. Smith |
| ______________________ |
| Janet C. Smith |
| Principal Financial Officer |
| <br>**Attachment A** |
| <br>Period (s) ended January 31, 2023<br>|
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;George Putnam Balanced Fund |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Putnam Growth Opportunities Fund |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Putnam Premier Income Trust |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Putnam Research Fund |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Putnam Ultra Short Duration Income Fund |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Putnam Short Term Investment Fund |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Putnam Strategic Intermediate Municipal Fund |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Putnam Tax-Free High Yield Fund |
| <br> Putnam Sustainable Retirement 2065 Fund |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Putnam Sustainable Retirement 2060 Fund |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Putnam Sustainable Retirement 2055 Fund |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Putnam Sustainable Retirement 2050 Fund |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Putnam Sustainable Retirement 2045 Fund |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Putnam Sustainable Retirement 2040 Fund |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Putnam Sustainable Retirement 2035 Fund |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Putnam Sustainable Retirement 2030 Fund |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Putnam Sustainable Retirement 2025 Fund |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Putnam Sustainable Retirement Maturity Fund |

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