Document:

EX-4.2

 Exhibit 4.2 

Execution Version 

R. R. DONNELLEY & SONS COMPANY 

and 
 U.S. BANK NATIONAL
ASSOCIATION, as Trustee 
  
  

FIRST SUPPLEMENTAL INDENTURE 

Dated as of June 18, 2020 

to 
 Indenture dated as
of June 18, 2020 
  
  

8.250% Notes due 2027 
  

 TABLE OF CONTENTS 

 

							
	Article I	  

	
	DEFINITIONS	  

			
	 Section 1.1
	 	 Generally
	  	 	4	 
	 Section 1.2
	 	 Definition of Certain Terms
	  	 	4	 
	
	Article II	  

	
	GENERAL TERMS OF THE NOTES	  

			
	 Section 2.1
	 	 Form and Legends
	  	 	7	 
	 Section 2.2
	 	 Amount and Payment of Principal and Interest
	  	 	10	 
	 Section 2.3
	 	 Denominations
	  	 	11	 
	 Section 2.4
	 	 Global Securities
	  	 	11	 
	 Section 2.5
	 	 Payments
	  	 	11	 
	 Section 2.6
	 	 Transfer and Exchange
	  	 	11	 
	 Section 2.7
	 	 Registrar and Paying Agent
	  	 	13	 
	 Section 2.8
	 	 Ranking
	  	 	13	 
	 Section 2.9
	 	 Events of Default
	  	 	13	 
	 Section 2.10
	 	 Trustee’s Right to Refuse Directions in Certain Circumstances
	  	 	13	 
	
	Article III	  

	
	REDEMPTION	  

			
	 Section 3.1
	 	 Redemption
	  	 	13	 
	 Section 3.2
	 	 Redemption Procedures
	  	 	14	 
	 Section 3.3
	 	 Notice of Redemption
	  	 	14	 
	
	Article IV	  

	
	CHANGE OF CONTROL	  

			
	 Section 4.1
	 	 Change of Control
	  	 	14	 
	
	Article V	  

	
	MISCELLANEOUS PROVISIONS	  

			
	 Section 5.1
	 	 Ratification of Base Indenture
	  	 	16	 
	 Section 5.2
	 	 Trustee Not Responsible for Recitals
	  	 	16	 
	 Section 5.3
	 	 Table of Contents, Headings, etc.
	  	 	17	 
	 Section 5.4
	 	 Counterpart Originals
	  	 	17	 
	 Section 5.5
	 	 Governing Law
	  	 	17	 

  
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 EXHIBIT A – FORM OF NOTE 

  
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 THIS FIRST SUPPLEMENTAL INDENTURE, dated as of June 18, 2020 (the “First
Supplemental Indenture”), between R. R. Donnelley & Sons Company, a Delaware corporation, as issuer (the “Company”), and U.S. Bank National Association, a national banking association, as trustee (the
“Trustee”). 
 RECITALS: 

WHEREAS, the Company has executed and delivered to the Trustee an Indenture, dated as of June 18, 2020 (the “Base Indenture”
and, as supplemented by this First Supplemental Indenture, the “Indenture”), providing for the issuance by the Company from time to time of its unsecured senior debentures, notes or other evidences of indebtedness to be issued in
one or more series unlimited as to principal amount (the “Securities”); 
 WHEREAS, the Company has duly authorized and
desires to cause to be established pursuant to the Base Indenture and this First Supplemental Indenture a new series of Securities designated the “8.250% Senior Notes due 2027” (the “Notes”), the form and terms of
such Notes to be set forth in this First Supplemental Indenture; 
 WHEREAS, all things necessary to make this First Supplemental Indenture
a valid agreement of the Company and the Trustee, in accordance with its terms, and a valid amendment of, and supplement to, the Base Indenture have been done; 

NOW, THEREFORE, in consideration of the premises and the purchase and acceptance of the Notes by the Holders thereof, the Company covenants
and agrees with the Trustee, for the equal and ratable benefit of the Holders, that the Base Indenture is supplemented and amended, to the extent expressed herein, as follows: 

ARTICLE I 

DEFINITIONS 

Section 1.1 Generally. 

(a) Capitalized terms used herein and not otherwise defined herein shall have the respective meanings ascribed thereto in the Base Indenture.

 (b) The rules of interpretation set forth in the Base Indenture shall be applied hereto as if set forth in full herein. 

Section 1.2 Definition of Certain Terms. For all purposes of this First Supplemental Indenture, except as otherwise expressly
provided or unless the context otherwise requires, the following terms shall have the following respective meanings: 
 “Adjusted
Treasury Rate” means, with respect to any Redemption Date, (x)(i) the weekly average for each Business Day during the most recent week that has ended at least three Business Days prior to the applicable Redemption Date of the yield to
maturity appearing in the most recently published statistical release designated “H.15” or any successor publication which is 

  
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published weekly by the Board of Governors of the Federal Reserve System and which establishes yields on actively traded United States Treasury securities adjusted to constant maturity under the
caption “Treasury Constant Maturities,” with a yield to maturity most nearly equal to the period from such Redemption Date to July 1, 2023; provided, however that if the period from such Redemption Date to July 1,
2023 is less than one year, the weekly average yield on actively traded United States Treasury securities adjusted to a constant maturity of one year will be used or (ii) if such release (or any successor release) is not published during the
week preceding the calculation date or does not contain such yields, the rate per year equal to the semi-annual equivalent yield to maturity of the applicable Comparable Treasury Issue (expressed as a percentage of its principal amount) equal to the
applicable Comparable Treasury Price for such Redemption Date, in each case calculated on the third Business Day immediately preceding the Redemption Date, plus (y) 0.50%. 

“Applicable Premium” means with respect to any Note at any applicable Redemption Date the excess of (if any) (A) the
present value at such Redemption Date of (1) the redemption price of such Note on July 1, 2023 (such redemption prices being set forth herein exclusive of any accrued interest) plus (2) all required remaining scheduled interest
payments due on such Note through July 1, 2023 (but not including accrued and unpaid interest to the applicable Redemption Date), computed using a discount rate equal to the applicable Adjusted Treasury Rate, over (B) the principal amount
of such Note on such Redemption Date 
 “Below Investment Grade Rating Event” means the Notes are rated below an Investment
Grade Rating by each of the Rating Agencies on the 60th day following the occurrence of a Change of Control (which date shall be extended if the rating of the Notes is under publicly announced consideration for possible downgrade by any of the
Rating Agencies on such 60th day, such extension to last until the date on which the Rating Agency considering such possible downgrade either (x) rates the Notes below an Investment Grade Rating or (y) publicly announces that it is no
longer considering the Notes for possible downgrade; provided, that no such extension shall occur if any of the Rating Agencies rates the Notes with an Investment Grade Rating that is not subject to review for possible downgrade on such 60th
day). 
 “Change of Control” means the occurrence of any of the following: (1) the direct or indirect sale, transfer,
conveyance or other disposition (other than by way of merger or consolidation), in one or a series of related transactions, of all or substantially all of the properties or assets of the Company and its Subsidiaries taken as a whole to any
“person” (as that term is used in Section 13(d)(3) of the Exchange Act) other than the Company or one of its Subsidiaries; (2) the consummation of any transaction (including, without limitation, any merger or consolidation) the
result of which is that any “person” (as that term is used in Section 13(d)(3) of the Exchange Act) becomes the beneficial owner, directly or indirectly, of more than 50% of the then outstanding number of shares of the Company’s
voting stock; or (3) the first day on which a majority of the members of the Company’s Board of Directors are not Continuing Directors. 

“Change of Control Offer” means an offer to repurchase Notes pursuant to Section 4.1 hereof. 

  
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 “Change of Control Payment” means, with respect to Notes tendered for
repurchase pursuant to a Change of Control Offer, an amount equal to 101% of the aggregate principal amount of such Notes plus accrued and unpaid interest thereon, if any, to the date of repurchase. 

“Change of Control Triggering Event” means the occurrence of both a Change of Control and a Below Investment Grade Rating
Event. 
 “Comparable Treasury Issue” means the United States Treasury security selected by the Quotation Agent as having a
maturity comparable to the remaining term of the Notes to be redeemed that would be utilized, at the time of selection and in accordance with customary financial practice, in pricing new issues of corporate debt securities of comparable maturity to
the remaining term of those Notes. 
 “Comparable Treasury Price” means, with respect to any Redemption Date, (1) the
average of the Reference Treasury Dealer Quotations for that Redemption Date, after excluding the highest and lowest Reference Treasury Dealer Quotations, or (2) if the Quotation Agent obtains fewer than four Reference Treasury Dealer
Quotations, the average of all Reference Treasury Dealer Quotations so received. 
 “Continuing Directors” means, as of any
date of determination, any member of the Board of Directors of the Company who (1) was a member of such Board of Directors on the date of the issuance of the Notes; or (2) was nominated for election or elected to such Board of Directors
with the approval of a majority of the Continuing Directors who were members of such Board of Directors at the time of such nomination or election (either by a specific vote or by approval of the Company’s proxy statement in which such member
was named as a nominee for election as a director, without objection to such nomination). 
 “Global Notes” means Notes
deposited with or on behalf of and registered in the name of the Depositary or its nominee, substantially in the form of Exhibit A and that bears the Global Note legend. 

“Initial Notes” means $244,949,000 aggregate principal amount of the Notes issued on the date hereof pursuant to a Company
Order and any Notes issued in replacement or substitution therefor in accordance with the provisions of the Indenture. 

“Investment Grade Rating” means a rating equal to or higher than Baa3 (or the equivalent) by Moody’s and BBB- (or the equivalent) by S&P. 
 “Moody’s” means Moody’s Investors
Service, Inc., a subsidiary of Moody’s Corporation, and its successors. 
 “Notes Custodian” means the custodian with
respect to the Global Notes (as appointed by the Depository), or any successor Person thereto and shall initially be the Registrar. 

“Person” means any individual, partnership, corporation, limited liability company, joint stock company, business trust,
trust, unincorporated association, joint venture or other entity, or a government or political subdivision or agency thereof. 

  
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 “Quotation Agent” means the Reference Treasury Dealer appointed by the
Company. 
 “Rating Agencies” means (1) each of Moody’s and S&P; and (2) if any of Moody’s or
S&P ceases to rate the Notes or fails to make a rating of the Notes publicly available for reasons outside of the Company’s control, a “nationally recognized statistical rating organization” within the meaning of
Section 3(a)(62) under the Exchange Act, selected by the Company (as certified by a resolution of the Company’s Board of Directors) as a replacement agency for Moody’s or S&P, or both of them, as the case may be. 

“Reference Treasury Dealer” means (1) each of BofA Securities, Inc., Citigroup Global Markets Inc., J.P. Morgan
Securities LLC, Goldman, Sachs & Co. LLC and Morgan Stanley & Co. LLC and their respective successors; provided, however, that if any of the foregoing shall cease to be a primary U.S. Government securities dealer in
New York City (a “Primary Treasury Dealer”), the Company shall substitute another Primary Treasury Dealer, and (2) any one other Primary Treasury Dealer selected by the Company. 

“Reference Treasury Dealer Quotations” means, with respect to each Reference Treasury Dealer and any Redemption Date, the
average, as determined by the Quotation Agent, of the bid and asked prices for the Comparable Treasury Issue (expressed in each case as a percentage of its principal amount) quoted in writing to the Quotation Agent by that Reference Treasury Dealer
at 5:00 p.m., New York City time, on the third Business Day preceding that Redemption Date. 
 “S&P” means
Standard & Poor’s Ratings Services, a division of The McGraw-Hill Companies, Inc., and its successors. 
 ARTICLE II

 GENERAL TERMS OF THE NOTES 

Section 2.1 Form and Legends.  

(a) The Notes and the Trustee’s certificates of authentication shall be substantially in the form of Exhibit A
to this First Supplemental Indenture, which are hereby incorporated into this First Supplemental Indenture. The terms and provisions contained in the Notes shall constitute, and are hereby expressly made, a part of this First Supplemental Indenture
and to the extent applicable, the Company and the Trustee, by their execution and delivery of this First Supplemental Indenture, expressly agree to such terms and provisions and to be bound thereby. 

(b) The Notes may have notations, legends or endorsements required by law, stock exchange rule or usage, in addition to those set forth on
Exhibit A and in this Section 2.1(b). The Company shall approve any notation, endorsement or legend on the Notes. 

  
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 (i) Each Global Note, whether or not an Initial Note, shall also bear the
following legend on the face thereof: 
 UNLESS THIS CERTIFICATE IS PRESENTED BY AN AUTHORIZED REPRESENTATIVE OF THE DEPOSITORY TRUST
COMPANY, A NEW YORK CORPORATION (“DEPOSITORY”) TO THE COMPANY OR ITS AGENT FOR REGISTRATION OF TRANSFER, EXCHANGE OR PAYMENT, AND ANY CERTIFICATE ISSUED IS REGISTERED IN THE NAME OF CEDE & CO. OR IN SUCH OTHER NAME AS IS REQUESTED
BY AN AUTHORIZED REPRESENTATIVE OF THE DEPOSITORY (AND ANY PAYMENT IS MADE TO CEDE & CO. OR TO SUCH OTHER ENTITY AS IS REQUESTED BY AN AUTHORIZED REPRESENTATIVE OF THE DEPOSITORY), ANY TRANSFER, PLEDGE OR OTHER USE HEREOF FOR VALUE OR
OTHERWISE BY OR TO ANY PERSON IS WRONGFUL INASMUCH AS THE REGISTERED OWNER HEREOF, CEDE & CO., HAS AN INTEREST HEREIN. 
 TRANSFERS
OF THIS GLOBAL NOTE SHALL BE LIMITED TO TRANSFERS IN WHOLE, BUT NOT IN PART, TO NOMINEES OF CEDE & CO. OR TO A SUCCESSOR THEREOF OR SUCH SUCCESSOR’S NOMINEE AND TRANSFERS OF PORTIONS OF THIS GLOBAL NOTE SHALL BE LIMITED TO TRANSFERS
MADE IN ACCORDANCE WITH THE RESTRICTIONS SET FORTH IN SECTION 2.1 OF THE FIRST SUPPLEMENTAL INDENTURE (AS DEFINED HEREIN). 
 (c)
Book-Entry Provisions. (i) This Section 2.1(c) shall apply only to Global Notes deposited with the Registrar, as custodian for the Depository. 

(i) Each Global Note initially shall (x) be registered in the name of the Depository or the nominee of the Depository,
(y) be delivered to the Notes Custodian for the Depository and (z) bear legends as set forth in Section 2.1(b). Transfers of a Global Note (but not a beneficial interest therein) will be limited to transfers
thereof in whole, but not in part, to the Depository, its successors or its respective nominees, except as set forth in Section 2.1(c)(iv) and 2.1(d). If a beneficial interest in a Global Note is transferred or
exchanged for a beneficial interest in another Global Note, the Notes Custodian will (x) record a decrease in the principal amount of the Global Note being transferred or exchanged equal to the principal amount of such transfer or exchange and
(y) record a like increase in the principal amount of the other Global Note. Any beneficial interest in one Global Note that is transferred to a Person who takes delivery in the form of an interest in another Global Note, or exchanged for an
interest in another Global Note, will, upon transfer or exchange, cease to be an interest in such Global Note and become an interest in the other Global Note and, accordingly, will thereafter be subject to all transfer and exchange restrictions, if
any, and other procedures applicable to beneficial interests in such other Global Note for as long as it remains such an interest. 

(ii) Members of, or participants in, the Depository (“Agent Members”) shall have no rights under this First
Supplemental Indenture with respect to any Global Note held on their behalf by Depository or by the Notes Custodian as the custodian of the Depository or under such Global Note, and Depository may be treated by the Company, the Trustee and any agent
of the Company or the Trustee as the absolute owner of such Global Note for all purposes whatsoever. Notwithstanding the foregoing, nothing herein shall prevent the Company, the Trustee or any agent of the Company or the Trustee from giving effect
to any written certification, proxy or other authorization furnished by the Depository or impair, as between the Depository and its Agent Members, the operation of customary practices of the Depository governing the exercise of the rights of a
holder of a beneficial interest in any Global Note. 

  
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 (iii) In connection with any transfer of a portion of the beneficial
interest in a Global Note pursuant to Section 2.1(c) to beneficial owners who are required to hold Definitive Notes, the Notes Custodian shall reflect on its books and records the date and a decrease in the principal amount
of such Global Note in an amount equal to the principal amount of the beneficial interest in the Global Note to be transferred, and the Company shall execute, and the Trustee shall authenticate and make available for delivery, one or more Definitive
Notes of like tenor and amount. 
 (iv) In connection with the transfer of an entire Global Note to beneficial owners
pursuant to Section 2.1(d), such Global Note shall be deemed to be surrendered to the Registrar for cancellation, and the Company shall execute, and the Trustee shall authenticate and make available for delivery, to each
beneficial owner identified by the Depository in exchange for its beneficial interest in such Global Note, an equal aggregate principal amount of Definitive Notes of authorized denominations. 

(v) The registered Holder of a Global Note may grant proxies and otherwise authorize any person, including Agent Members and
persons that may hold interests through Agent Members, to take any action which a Holder is entitled to take under this First Supplemental Indenture or the Notes. 

(vi) Any Holder of a Global Note shall, by acceptance of such Global Note, agree that transfers of beneficial interests in such
Global Note may be effected only through a book-entry system maintained by (i) the Holder of such Global Note (or its agent) or (ii) any holder of a beneficial interest in such Global Note, and that ownership of a beneficial interest in
such Global Note shall be required to be reflected in a book entry. 
 (d) Except as provided below, owners of beneficial interests in Global
Notes will not be entitled to receive Definitive Notes. Definitive Notes shall be transferred to all beneficial owners in exchange for their beneficial interests in a Global Note if (A) the Depository notifies the Company that it is unwilling
or unable to continue as depositary for such Global Note or the Depository ceases to be a clearing agency registered under the Exchange Act, at a time when the Depository is required to be so registered in order to act as depositary, and in each
case a successor depositary is not appointed by the Company or (B) an Event of Default has occurred and is continuing. In the event of the occurrence of any of the events specified in clause (A) or (B) of the preceding sentence,
the Company shall promptly make available to the Trustee or the authenticating agent a reasonable supply of Definitive Notes. If required to do so pursuant to any applicable law or regulation, beneficial owners may also obtain Definitive Notes in
exchange for their beneficial interests in a Global Note upon written request in accordance with the Depository’s and the Registrar’s procedures. 

  
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 (i) If a Definitive Note is transferred or exchanged for a beneficial
interest in a Global Note, the Registrar will (x) cancel such Definitive Note, (y) record an increase in the principal amount of such Global Note equal to the principal amount of such transfer or exchange and (z) in the event that
such transfer or exchange involves less than the entire principal amount of the canceled Definitive Note, the Company shall execute, and the Trustee shall authenticate and make available for delivery, to the transferring Holder a new Definitive Note
representing the principal amount not so transferred. 
 (ii) If a Definitive Note is transferred or exchanged for another
Definitive Note, (x) the Registrar will cancel the Definitive Note being transferred or exchanged, (y) the Company shall execute, and the Trustee shall authenticate and make available for delivery, one or more new Definitive Notes in
authorized denominations having an aggregate principal amount equal to the principal amount of such transfer or exchange to the transferee (in the case of a transfer) or the Holder of the canceled Definitive Note (in the case of an exchange),
registered in the name of such transferee or Holder, as applicable, and (z) if such transfer or exchange involves less than the entire principal amount of the canceled Definitive Note, the Company shall execute, and the Trustee shall
authenticate and make available for delivery to the Holder thereof, one or more Definitive Notes in authorized denominations having an aggregate principal amount equal to the untransferred or unexchanged portion of the canceled Definitive Notes,
registered in the name of the Holder thereof. 
 Section 2.2 Amount and Payment of Principal and Interest. 

(a) The Trustee shall authenticate and deliver the Initial Notes for original issue on the date hereof in the aggregate principal amount of
$244,949,000 pursuant to a Company Order. The principal amount of each Note shall be payable on July 1, 2027. 
 (b) The Notes shall
bear interest at 8.250% per year beginning on the date of issuance until the Notes are redeemed, paid, or duly provided for. Interest shall be paid semi-annually in arrears on January 1 and July 1 of each year (each an “Interest
Payment Date”), commencing on January 1, 2021. The regular record date for interest payable on the Notes shall be the December 15 and June 15, as the case may be, immediately preceding each Interest Payment Date. Interest
will be computed on the basis of a 360-day year comprised of twelve 30-day months. Any payment of principal or interest required to be made on a day that is not a
Business Day need not be made on such day, but may be made on the next succeeding Business Day with the same force and effect as if made on such day and no interest shall accrue as a result of such delayed payment. 

(c) Subject to the terms and conditions contained herein, the Company may from time to time, without the consent of the existing Holders create
and issue additional Notes (the “Additional Notes”) having the same terms and conditions as the Notes in all respects, except for issue date and the first payment of interest thereon. Such Additional Notes, at the Company’s
determination and in accordance with the provisions of the Indenture, will be consolidated with and form a single series with the previously outstanding Notes for all purposes under the Indenture, including, without limitation, amendments, waivers
and redemptions; provided that Additional Notes will not be issued with the same CUSIP or ISIN, as applicable, as existing Notes unless such Additional Notes are fungible with the existing Notes for U.S. federal

  
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income tax purposes. Holders of the Initial Notes and the Additional Notes will vote and consent together on all matters to which such Holders are entitled to vote or consent as one class, and
none of the Holders of the Initial Notes or the Additional Notes shall have the right to vote or consent as a separate class on any matter to which such Holders are entitled to vote or consent. The aggregate principal amount of the Additional Notes,
if any, shall be unlimited. 
 Section 2.3 Denominations. The Notes will be issuable only in fully registered form without
coupons in denominations of $2,000 and any integral multiples of $1,000 in excess thereof. 
 Section 2.4 Global Securities. The
Notes will be issuable in the form of one or more Global Securities and the Depository for such Global Securities will be The Depository Trust Company in accordance with the Base Indenture. 

Section 2.5 Payments. The principal and interest on Notes represented by Global Securities will be payable to the Depository or
its nominee, as the case may be, as the sole registered owner and the sole Holder of the Global Securities represented thereby. The principal and interest on Notes represented by Physical Securities will be payable, either in person or by mail, at
the office of the Paying Agent. 
 Section 2.6 Transfer and Exchange. 

(a) Transfers of Global Securities will be limited to transfer in whole, but not in part, to the Depository, its successors or their respective
nominees. Interests of beneficial owners in the Global Securities may be transferred or exchanged for Physical Securities in accordance with the Indenture. If Notes represented by Physical Securities are presented to the Registrar with a request
from the Holder of such Securities to register a transfer or to exchange them for an equal principal amount of Securities of other authorized denominations, the Registrar will register the transfer as requested in accordance with the Indenture. 

(b) A Holder may transfer a Note (or a beneficial interest therein) to another Person or exchange a Note (or a beneficial interest therein) for
another Note or Notes of any authorized denomination in accordance with this Supplemental Indenture. The Registrar will promptly register any transfer or exchange that meets the requirements hereof by noting the same in the Notes register maintained
by the Registrar. The transfer or exchange of any Note (or a beneficial interest therein) may only be made in accordance with this Section 2.6 and Section 2.1(c) and 2.1(d), as applicable,
and, in the case of a Global Note (or a beneficial interest therein), the applicable rules and procedures of the Depository. 
 (c) To permit
registrations of transfers and exchanges, the Company shall, subject to the other terms and conditions of this Article II, execute and the Trustee shall authenticate Definitive Notes and Global Notes at the Company’
and Registrar’s written request. 
 (d) No service charge shall be made to a Holder for any registration of transfer or exchange, but
the Company and the Trustee may require the Holder to pay a sum sufficient to cover any transfer tax assessments or similar governmental charge payable in connection therewith (other than any such transfer taxes, assessments or similar governmental
charges payable upon exchange or transfer pursuant to Sections 2.2 or 2.6 of this First Supplemental Indenture or Sections 2.08, 2.11, 3.07 or 8.05 of the Base Indenture). 

  
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 (e) The Company (and the Registrar) shall not be required to register the transfer of or
exchange of any Note (A) for a period beginning (1) 15 calendar days before the mailing of a notice of an offer to repurchase or redeem Notes and ending at the close of business on the day of such mailing or (2) 15 calendar
days before an interest payment date and ending on such interest payment date or (B) called for redemption, except the unredeemed portion of any Note being redeemed in part. 

(f) Prior to the due presentation for registration of transfer of any Note, the Company, the Trustee, the Paying Agent or the Registrar may
deem and treat the person in whose name a Note is registered as the owner of such Note for the purpose of receiving payment of principal of, premium, if any, and (subject to paragraph 2 of the form of Notes attached hereto as Exhibit A)
interest on such Note and for all other purposes whatsoever, including without limitation the transfer or exchange of such Note, whether or not such Note is overdue, and none of the Company, the Trustee, the Paying Agent or the Registrar shall be
affected by notice to the contrary. 
 (g) All Notes issued upon any transfer or exchange pursuant to the terms of this First Supplemental
Indenture shall evidence the same debt and shall be entitled to the same benefits under this First Supplemental Indenture as the Notes surrendered upon such transfer or exchange. 

(h) Neither the Trustee nor the Registrar shall have any responsibility or obligation to any beneficial owner of a Global Note, a member of, or
a participant in, the Depository or other Person with respect to the accuracy of the records of the Depository or its nominee or of any participant or member thereof, with respect to any ownership interest in the Notes or with respect to the
delivery to any participant, member, beneficial owner or other Person (other than the Depository) of any notice (including any notice of redemption or purchase) or the payment of any amount or delivery of any Notes (or other security or property)
under or with respect to such Notes. All notices and communications to be given to the Holders and all payments to be made to Holders in respect of the Notes shall be given or made only to or upon the order of the registered Holders (which shall be
the Depository or its nominee in the case of a Global Note). The rights of beneficial owners in any Global Note shall be exercised only through the Depository subject to the applicable rules and procedures of the Depository. The Trustee may rely and
shall be fully protected in relying upon information furnished by the Depository with respect to its members, participants and any beneficial owners. 

(i) Neither the Trustee nor the Registrar shall have any obligation or duty to monitor, determine or inquire as to compliance with any
restrictions on transfer imposed under this First Supplemental Indenture or under applicable law with respect to any transfer of any interest in any Note (including any transfers between or among Depository participants, members or beneficial owners
in any Global Note) other than to require delivery of such certificates and other documentation or evidence as are expressly required by, and to do so if and when expressly required by, the terms of this First Supplemental Indenture, and to examine
the same to determine substantial compliance as to form with the express requirements hereof. Neither the Trustee, the Registrar nor any of their respective agents shall have any responsibility for any actions taken or not taken by the Depository.

  
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 Section 2.7 Registrar and Paying Agent. The Company initially appoints the
Trustee as Registrar and Paying Agent. The Company may change the Paying Agent and Registrar without notice to Holders. 
 Section 2.8
Ranking. The Notes will be senior unsecured obligations of the Company. The payment of the principal of, premium, if any, and interest on the Notes will (i) rank equally in right of payment with all other indebtedness of the Company that
is not by its terms expressly subordinated to other indebtedness of the Company, and (ii) rank senior in right of payment to all indebtedness of the Company that is, by its terms, expressly subordinated to the senior indebtedness of the
Company. 
 Section 2.9 Events of Default. With respect to the Notes, Section 6.02 of the Base Indenture shall be amended
by deleting from the parenthetical contained in the first sentence of Section 6.02 the phrase “an Event of Default specified in Section 6.01(3) with respect to Section 4.09 or” and such phrase shall not be applicable to the
Notes. 
 Section 2.10 Trustee’s Right to Refuse Directions in Certain Circumstances. With respect to
directions given by the Holders of a majority in principal amount pursuant to the Indenture to the Trustee in its exercise of any trust or power, the Trustee will be entitled to refuse to follow any such direction that conflicts with law or the
Indenture or that the Trustee determines in good faith is unduly prejudicial to the rights of other Holders or could, in reasonable likelihood, impose personal liability upon the Trustee, unless the Trustee is offered indemnity satisfactory to it.

 ARTICLE III 

REDEMPTION 

Section 3.1 Redemption. 

(a) Except as provided in this Article III, the Company shall have no obligation to redeem, purchase or repay the Notes pursuant to any
mandatory redemption, sinking fund or analogous provisions or at the option of a Holder thereof. 
 (b) Except as set forth below, the
Company will not be entitled to redeem the Notes at its option prior to July 1, 2023. 
 (c) On and after July 1, 2023, the Company
may at its option on one or more occasions redeem all or a portion of the Notes at the redemption prices (expressed in percentages of principal amount on the Redemption Date), plus accrued and unpaid interest to, but not including, the Redemption
Date, if redeemed during the 12-month period commencing on July 1 of the years set forth below: 
  

					
	 Period
	  	Redemption
Price	 
	 2023
	  	 	106.188	% 
	 2024
	  	 	104.125	% 
	 2025
	  	 	102.063	% 
	 2026 and thereafter
	  	 	100.000	% 

  
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 (d) Prior to July 1, 2023, the Company may at its option to redeem all or a portion of
the Notes at a redemption price equal to 100% of the principal amount of the Notes to be redeemed plus the Applicable Premium as of, and accrued and unpaid interest to, but not including, the Redemption Date. 

Section 3.2 Redemption Procedures. The Trustee will select Notes called for redemption in part on a pro rata basis or on as nearly
a pro rata basis as is practicable (subject to procedures of the Depository); provided that Notes in principal amounts of $2,000 or less shall be redeemed in whole and not in part. In the case of Notes represented by Physical Securities, a
new Note in principal amount equal to the unredeemed portion thereof will be issued in the name of the Holder thereof upon cancellation of the original Note. In the case of Notes represented by a Global Security, the outstanding principal amount of
the Global Security representing the Notes will be reduced by book-entry. Notes called for redemption become due on the Redemption Date. On and after the Redemption Date, interest stops accruing on Notes or portions of them called for redemption
(unless there is a default in the payment thereof). 
 Section 3.3 Notice of Redemption. 

(a) At the Company’s written request made at least three Business Days prior to the date on which notice is to be given (or such shorter
period as may be agreed to by the Trustee), the Trustee shall give the notice of redemption in the Company’s name and at the Company’s sole expense. 

(b) Notices of redemption shall be mailed by first class mail at least 10 but not more than 60 days before the Redemption Date to each Holder
of Notes to be redeemed at its registered address. If any Note is to be redeemed in part only, the notice of redemption that relates to such Note shall state the portion of the principal amount thereof to be redeemed. 

(c) Any notice to holders of Notes of any redemption will include the appropriate calculation of the Redemption Price, but does not need to
include the Redemption Price itself. The actual Redemption Price, calculated as described above, will be set forth in an Officers’ Certificate of the Company delivered to the Trustee no later than two Business Days prior to the Redemption Date

 ARTICLE IV 

CHANGE OF CONTROL 

Section 4.1 Change of Control. 

(a) Upon the occurrence of a Change of Control Triggering Event, unless all Notes have been called for redemption, each Holder of Notes shall
have the right to require the Company to repurchase all or any part (equal to $2,000 or an integral multiple of $1,000 in excess thereof) of such Holder’s Notes at an offer price in cash equal to the Change of Control Payment. 

  
 14 

 (b) Within 30 days following any Change of Control Triggering Event, the Company shall mail,
or cause to be mailed, a notice to the Trustee and to each Holder describing the transaction or transactions that constitute the Change of Control Triggering Event and specifying: 

(i) that the Change of Control Offer is being made pursuant to this Section 4.1 and that all Notes tendered will be
accepted for payment; 
 (ii) the Change of Control Payment and the purchase date, which shall be a Business Day no earlier
than 10 days and no later than 60 days from the date such notice is mailed (the “Change of Control Payment Date”); 

(iii) the CUSIP number for the Notes; 

(iv) that any Note not tendered will continue to accrue interest; 

(v) that, unless the Company defaults in the payment of the Change of Control Payment, all Notes accepted for payment pursuant
to the Change of Control Offer will cease to accrue interest after the Change of Control Payment Date; 
 (vi) that Holders
electing to have any Notes purchased pursuant to a Change of Control Offer will be required to surrender such Notes to the Paying Agent at the address specified in the notice prior to the close of business on the third Business Day preceding the
Change of Control Payment Date; 
 (vii) that Holders will be entitled to withdraw their election referred to in clause
(vi) if the Paying Agent receives, not later than the close of business on the second Business Day preceding the Change of Control Payment Date, a facsimile transmission or letter setting forth the name of the Holder, the principal amount of
Notes delivered for purchase, and a statement that such Holder is withdrawing his election to have the Notes purchased; and 

(viii) that Holders whose Notes are being purchased only in part will be issued new Notes equal in principal amount to the
unpurchased portion of the Notes surrendered, which unpurchased portion will be equal to $2,000 in principal amount or an integral multiple of $1,000 in excess thereof. 

(c) The Company shall cause the Change of Control Offer to remain open for at least 20 Business Days or such longer period as is required by
applicable law. The Company shall comply with the requirements of Rule 14e-1 under the Exchange Act and any other securities laws and regulations thereunder to the extent those laws and regulations are
applicable in connection with the repurchase of the Notes as a result of a Change of Control Triggering Event. To the extent that the provisions of any securities laws or regulations conflict with the provisions of this Section 4.1, the Company
will comply with the applicable securities laws and regulations and will not be deemed to have breached its obligations under this Section 4.1 by virtue of such conflict. 

  
 15 

 (d) On the Change of Control Payment Date, the Company will, to the extent lawful: 

(i) accept for payment all Notes or portions thereof properly tendered pursuant to the Change of Control Offer; 

(ii) deposit with the Paying Agent an amount equal to the Change of Control Payment in respect of all Notes or portions of
Notes properly tendered; and 
 (iii) deliver or cause to be delivered to the Trustee the Notes properly accepted together
with an Officers’ Certificate stating the aggregate principal amount of Notes or portions of Notes being purchased by the Company. 

(e) The Paying Agent will promptly mail to each Holder of Notes properly tendered the Change of Control Payment for such Notes, and the Trustee
will promptly authenticate and mail (or cause to be transferred by book entry) to each Holder a new Note equal in principal amount to any unpurchased portion of the Notes surrendered, if any; provided that each new Note will be in a principal
amount of $2,000 or an integral multiple of $1,000 in excess thereof. The Company will publicly announce the results of the Change of Control Offer on or as soon as practicable after the Change of Control Payment Date. 

(f) The Company shall not be required to make a Change of Control Offer upon a Change of Control Triggering Event if a third party makes the
Change of Control Offer in the manner, at the times and otherwise in compliance with the requirements set forth in this Section 4.1 applicable to a Change of Control Offer made by the Company and purchases all Notes properly tendered and not
withdrawn under such Change of Control Offer. 
 (g) The Company may make a Change of Control Offer in advance of, but conditioned on, the
occurrence of a Change of Control Triggering Event but otherwise in accordance with the provisions of this Section 4.1. 

ARTICLE V 

MISCELLANEOUS PROVISIONS 

Section 5.1 Ratification of Base Indenture. The Base Indenture, as supplemented by this First Supplemental Indenture, is in all
respects ratified and confirmed, and this First Supplemental Indenture shall be deemed part of the Base Indenture in the manner and to the extent herein and therein provided. 

Section 5.2 Trustee Not Responsible for Recitals. The recitals contained herein and in the Notes, except with respect to the
Trustee’s certificates of authentication, shall be taken as the statements of the Company, and the Trustee assumes no responsibility for the correctness of the same. The Trustee makes no representations as to the validity or sufficiency of this
First Supplemental Indenture or of the Notes. 

  
 16 

 Section 5.3 Table of Contents, Headings, etc. The table of contents and headings
of the Articles and Sections of this First Supplemental Indenture have been inserted for convenience of reference only, are not to be considered a part hereof and shall in no way modify or restrict any of the terms or provisions hereof. 

Section 5.4 Counterpart Originals. The parties may sign any number of copies of this First Supplemental Indenture. Each signed
copy shall be an original, but all of them together represent the same agreement. The exchange of copies of this First Supplemental Indenture and of signature pages by facsimile or PDF transmission shall constitute effective execution and delivery
of this First Supplemental Indenture as to the parties hereto and may be used in lieu of the original First Supplemental Indenture for all purposes. Signatures of the parties hereto transmitted by facsimile or PDF shall be deemed to be their
original signatures for all purposes. All notices, approvals, consents, requests and any communications hereunder must be in writing (provided that any communication sent to Trustee hereunder must be in the form of a document that is signed manually
or by way of a digital signature provided by DocuSign (or such other digital signature provider as specified in writing to Trustee by the authorized representative), in English. Company agrees to assume all risks arising out of the use of using
digital signatures and electronic methods to submit communications to Trustee, including without limitation the risk of Trustee reasonably acting on unauthorized instructions, and the risk of interception and misuse by third parties. 

Section 5.5 Governing Law. THIS FIRST SUPPLEMENTAL INDENTURE AND THE NOTES SHALL BE GOVERNED BY AND CONSTRUED IN ACCORDANCE WITH
THE LAWS OF THE STATE OF NEW YORK. 
 [Signature Pages Follow] 

  
 17 

 IN WITNESS WHEREOF, the parties have caused this First Supplemental Indenture to be duly
executed all as of the date and year first written above. 
  

			
	R. R. DONNELLEY & SONS COMPANY
		
	By:	 	 /s/ Terry D. Peterson

	Name:	 	Terry D. Peterson
	Title:	 	Executive Vice President and Chief Financial Officer

 [Signature Page to RRD First Supplemental Indenture] 

 
			
	U.S. BANK NATIONAL ASSOCIATION, as Trustee
		
	By:	 	 /s/ Richard Prokosch

	Name:	 	Richard Prokosch
	Title:	 	Vice President

 [Signature Page to RRD First Supplemental Indenture] 

 EXHIBIT A 

Form of Note 
 UNLESS THIS CERTIFICATE IS
PRESENTED BY AN AUTHORIZED REPRESENTATIVE OF THE DEPOSITORY TRUST COMPANY, A NEW YORK CORPORATION (“DEPOSITORY”) TO THE COMPANY OR ITS AGENT FOR REGISTRATION OF TRANSFER, EXCHANGE OR PAYMENT, AND ANY CERTIFICATE ISSUED IS REGISTERED IN THE
NAME OF CEDE & CO. OR IN SUCH OTHER NAME AS IS REQUESTED BY AN AUTHORIZED REPRESENTATIVE OF THE DEPOSITORY (AND ANY PAYMENT IS MADE TO CEDE & CO. OR TO SUCH OTHER ENTITY AS IS REQUESTED BY AN AUTHORIZED REPRESENTATIVE OF THE
DEPOSITORY), ANY TRANSFER, PLEDGE OR OTHER USE HEREOF FOR VALUE OR OTHERWISE BY OR TO ANY PERSON IS WRONGFUL INASMUCH AS THE REGISTERED OWNER HEREOF, CEDE & CO., HAS AN INTEREST HEREIN. 

TRANSFERS OF THIS GLOBAL NOTE SHALL BE LIMITED TO TRANSFERS IN WHOLE, BUT NOT IN PART, TO NOMINEES OF CEDE & CO. OR TO A SUCCESSOR THEREOF OR SUCH
SUCCESSOR’S NOMINEE AND TRANSFERS OF PORTIONS OF THIS GLOBAL NOTE SHALL BE LIMITED TO TRANSFERS MADE IN ACCORDANCE WITH THE RESTRICTIONS SET FORTH IN SECTION 2.1 OF THE FIRST SUPPLEMENTAL INDENTURE (AS DEFINED HEREIN). 

  
 A-1 

 CUSIP No.: 257867 BE0 

ISIN No.: US257867BE01 
 R. R.
DONNELLEY & SONS COMPANY 
 8.250% NOTE DUE 2027 
  

					
	 No. _____
	  	$	_________	 

 R. R. DONNELLEY & SONS COMPANY, a Delaware corporation, as issuer (the “Company”), for
value received, promises to pay to CEDE & CO. or registered assigns the principal sum of $____________ on July 1, 2027. 

Interest Payment Dates: January 1 and July 1, commencing January 1, 2021 

Record Dates: December 15 and June 15. 

Reference is made to the further provisions of this Note contained herein, which will for all purposes have the same effect as if set forth at
this place. 

  
 A-2 

 IN WITNESS WHEREOF, the Company has caused this Note to be signed manually or by facsimile
by one of its duly authorized officers. 
  

			
	R. R. DONNELLEY & SONS COMPANY
		
	By:	 	              

		 	Name:
		 	Title:

  
 A-3 

 Certificate of Authentication 

This is one of the 8.250% Notes due 2027 referred to in the within-mentioned Indenture. 

 

			
	U.S. BANK NATIONAL ASSOCIATION, as Trustee
		
	By:	 	
                     
    

		 	Authorized Signatory

 Dated: ___________, 20__ 

  
 A-4 

 [FORM OF REVERSE OF NOTE] 

R. R. DONNELLEY & SONS COMPANY 

8.250% NOTE DUE 2027 
 1.
Interest. R. R. DONNELLEY & SONS COMPANY, a Delaware corporation, as issuer (the “Company”), promises to pay, until the principal hereof is paid or made available for payment, interest on the principal amount set forth on
the face hereof at a rate of 8.250% per annum. Interest hereon will accrue from and including the most recent date to which interest has been paid or, if no interest has been paid, from and including June 18, 2020 to but excluding the date on
which interest is paid. Interest shall be payable in arrears on January 1 and July 1 of each year, commencing January 1, 2021. Interest will be computed on the basis of a 360-day year comprised
of twelve 30-day months. The Company shall pay interest on overdue principal and on overdue interest (to the full extent permitted by law) at the rate borne by the Notes. 

2. Method of Payment. The Company will pay interest hereon (except defaulted interest) to the Persons who are registered Holders at the
close of business on the December 15 and June 15 immediately preceding the interest payment date (whether or not a Business Day). Holders do not have to surrender Notes to a Paying Agent to collect principal payments. The Company will pay
to the Paying Agent principal and interest in money of the United States of America that at the time of payment is legal tender for payment of public and private debts. If a Holder has given wire transfer instructions to the Company, the Company
will pay, or cause to be paid by the Paying Agent, all principal (and premium, if any) and interest on that Holder’s Notes in accordance with those instructions. All other payments on the Notes will be made at the office or agency of the Paying
Agent and Registrar unless the Company elects to make interest payments by check mailed to the Holders at their address set forth in the register of Holders. 

3. Paying Agent and Registrar. Initially, U.S. Bank National Association (the “Trustee”) will act as a Paying Agent and
Registrar. The Company may change any Paying Agent or Registrar without notice to the Holders. The Company or any of its Subsidiaries may act as Paying Agent or Registrar. 

4. Indenture. This Note is one of the series designated on the face hereof. This Note is one of a duly authorized issue of securities of
the Company issued and to be issued in one or more series under an Indenture dated as of June 18, 2020 (the “Base Indenture”), between the Company and the Trustee, as supplemented by the First Supplemental Indenture, dated as of
June 18, 2020, between the Company and the Trustee (the “First Supplemental Indenture” and, together with the Base Indenture, the “Indenture”). This is one of an issue of Notes of the Company issued, or to be
issued, under the Indenture. The terms of the Notes include those stated in the Indenture and those made part of the Indenture by reference to the Trust Indenture Act of 1939 (15 U.S. Code §§ 77aaa-77bbbb), as amended from time to
time (the “Trust Indenture Act”). The Notes are subject to all such terms, and Holders are referred to the Indenture and the Trust Indenture Act for a statement of them. Capitalized and certain other terms used herein and not
otherwise defined have the meanings set forth in the Indenture. To the extent any provision of this Note conflicts with the express provisions of the Indenture, the provisions of the Indenture shall govern and be controlling. 

  
 A-5 

 5. Optional Redemption. 

(a) Except as set forth below, the Company will not be entitled to redeem the Notes at its option prior to July 1, 2023. 

(b) On and after July 1, 2023, the Company may at its option on one or more occasions redeem all or a portion of the Notes at the
redemption prices (expressed in percentages of principal amount on the Redemption Date, plus accrued and unpaid interest to, but not including, the Redemption Date, if redeemed during the 12-month period
commencing on July 1 of the years set forth below: 
  

					
	 Period
	  	Redemption Price	 
	 2023
	  	 	106.188	% 
	 2024
	  	 	104.125	% 
	 2025
	  	 	102.063	% 
	 2026 and thereafter
	  	 	100.000	% 

 (c) Prior to July 1, 2023, the Company may at its option to redeem all or a portion of the Notes at a
redemption price equal to 100% of the principal amount of the Notes to be redeemed plus the Applicable Premium as of, and accrued and unpaid interest to, but not including, the Redemption Date. 

(d) The Company may provide in such notice that payment of such price and performance of the Company’s obligations with respect to such
redemption or purchase may be performed by another Person. Any such notice may, at the Company’s discretion, be subject to the satisfaction of one or more conditions precedent. 

(e) Any notice to holders of Notes of a redemption pursuant to paragraph 5 hereof will include the appropriate calculation of the Redemption
Price, but does not need to include the Redemption Price itself. The actual Redemption Price, calculated as described above, will be set forth in an Officers’ Certificate of the Company delivered to the Trustee no later than two Business Days
prior to the Redemption Date. 
 6. Redemption Procedures. The Trustee will select Notes called for redemption in part pursuant to
paragraph 5 on a pro rata basis (or on as nearly a pro rata basis as is practicable), by lot or any other method that the Trustee deems to be fair and appropriate (subject to procedures of the Depository); provided that no Notes
of $2,000 or less shall be redeemed in part. A new Note in principal amount equal to the unredeemed portion thereof will be issued in the name of the Holder thereof upon cancellation of the original Note, or in the case of Notes represented by a
Global Security, the outstanding principal amount of such Global Security will be reduced by book-entry. Notes called for redemption pursuant to paragraph 5 hereto become due on the Redemption Date. On and after the Redemption Date, interest stops
accruing on Notes or portions of them called for redemption (unless there is a default in the payment thereof). 
 7. Notice of
Redemption. Notices of redemption pursuant to paragraph 5 shall be mailed by first class mail at least 10 but not more than 60 days before the Redemption Date to each Holder of Notes to be redeemed at its registered address. If any Note is to be
redeemed in part only, the notice of redemption that relates to such Note shall state the portion of the principal amount thereof to be redeemed. 

  
 A-6 

 8. Change of Control. Upon the occurrence of a Change of Control Triggering Event,
unless all Notes have been called for redemption pursuant to paragraph 5 of this Note, each Holder of Notes of this series shall have the right to require the Company to repurchase all or any part (equal to $2,000 or an integral multiple of $1,000
in excess thereof) of such Notes at an offer price in cash equal to the Change of Control Payment. The Change of Control Offer will be made in accordance with the terms specified in the Indenture. 

9. Denominations, Transfer, Exchange. The Notes are in registered form without coupons in denominations of $2,000 and integral multiples
of $1,000 in excess thereof. A Holder may transfer or exchange Notes in accordance with the Indenture. The Registrar may require a Holder, among other things, to furnish appropriate endorsements and transfer documents and to pay to it any taxes and
fees required by law or permitted by the Indenture. 
 10. Persons Deemed Owners. The registered Holder of this Note may be treated as
the owner of this Note for all purposes. 
 11. Unclaimed Money. If money for the payment of principal or interest remains unclaimed
for two years, the Trustee or Paying Agent will pay the money back to the Company at its written request. After that, Holders entitled to the money must look to the Company for payment as general creditors unless an “abandoned property”
law designates another Person. 
 12. Amendment, Supplement, Waiver, Etc. The Company and the Trustee (if a party thereto) may,
without the consent of the Holders of any outstanding Notes, amend, waive or supplement the Indenture or the Notes for certain specified purposes, including, among other things, curing ambiguities, defects or inconsistencies, maintaining the
qualification of the Indenture under the Trust Indenture Act, providing for the assumption by a successor to the Company of its obligations under the Indenture and making any change that does not materially and adversely affect the rights of any
Holder. Other amendments and modifications of the Indenture or the Notes may be made by the Company and the Trustee with the consent of the Holders of not less than a majority of the aggregate principal amount of the outstanding Notes, subject to
certain exceptions requiring the consent of the Holders of the particular Notes to be affected. 
 13. Successor Corporation. When a
successor corporation assumes all the obligations of its predecessor under the Notes and the Indenture and the transaction complies with the terms of Article Five of the Base Indenture, the predecessor corporation will, except as provided in Article
Five of the Base Indenture, be released from those obligations. 
 14. Defaults and Remedies. Events of Default are set forth in the
Indenture. Subject to certain limitations in the Indenture, if an Event of Default (other than an Event of Default specified in Sections 6.01(4) and 6.01(5) of the Base Indenture) occurs and is continuing, then, and in each and every such case,
either the Trustee, by notice in writing to the Company, or the Holders of not less than 25% of the principal amount of the Notes then outstanding, by notice in writing to the Company and the Trustee, may, and the Trustee at the request of such
Holders 

  
 A-7 

 
shall, declare due and payable, if not already due and payable, the principal of and any accrued and unpaid interest on all of the Notes; and upon any such declaration all such amounts upon such
Notes shall become and be immediately due and payable, anything in the Indenture or in the Notes to the contrary notwithstanding. If an 

Event of Default specified in Sections 6.01(4) and 6.01(5) of the Base Indenture occurs, then the principal of and any accrued and unpaid
interest on all of the Notes shall immediately become due and payable without any declaration or other act on the part of the Trustee or any Holder. Holders may not enforce the Indenture or the Notes except as provided in the Indenture. The Trustee
may require indemnity satisfactory to it before it enforces the Indenture or the Notes. Subject to certain limitations, Holders of a majority in principal amount of the then outstanding Notes may direct the Trustee in its exercise of any trust or
power, provided, that the Trustee will be entitled to refuse to follow any such direction that conflicts with law or the Indenture or that the Trustee determines in good faith is unduly prejudicial to the rights of other Holders or could, in
reasonable likelihood, impose personal liability upon the Trustee, unless the Trustee is offered indemnity satisfactory to it. The Trustee may withhold from Holders notice of any continuing default (except a default in payment of principal, premium,
if any, or interest on the Notes or a default in the observance or performance of any of the obligations of the Company under Article Five of the Base Indenture) if it determines that withholding notice is in their best interests. 

15. Trustee Dealings with Company. Subject to certain limitations imposed by the Trust Indenture Act, the Trustee, in its individual or
any other capacity, may make loans to, accept deposits from, and perform services for the Company or its Affiliates, and may otherwise deal with the Company or its Affiliates, as if it were not Trustee. 

16. No Recourse Against Others. No past, present or future director, officer, employee, incorporator, agent, member or stockholder or
Affiliate of the Company, as such, shall have any liability for any obligations of the Company under the Notes, the Indenture or for any claim based on, in respect of, or by reason of, such obligations or their creation. Each Holder of Notes by
accepting a Note waives and releases all such liabilities. The waiver and release are part of the consideration for issuance of the Notes. 

17. Discharge. The Company’s obligations pursuant to the Indenture will be discharged, except for obligations pursuant to certain
sections thereof, subject to the terms of the Indenture, upon the payment of all the Notes or upon the irrevocable deposit with the Trustee of United States dollars or Government Obligations sufficient to pay when due principal of and interest on
the Notes to maturity or redemption. 
 18. Authentication. This Note shall not be valid until the Trustee signs the certificate of
authentication on the other side of this Security. 
 19. Governing Law. THIS NOTE SHALL BE GOVERNED BY AND CONSTRUED IN ACCORDANCE
WITH THE LAWS OF THE STATE OF NEW YORK. The Trustee and the Company agree to submit to the jurisdiction of the courts of the State of New York in any action or proceeding arising out of or relating to the Indenture or the Notes. 

  
 A-8 

 20. Abbreviations. Customary abbreviations may be used in the name of a Holder or an
assignee, such as: TEN COM (= tenants in common), TENANT (= tenants by the entireties), JT TEN (= joint tenants with right of survivorship and not as tenants in common), CUST (= Custodian), and U/G/M/A (= Uniform Gifts to Minors Act). 

The Company will furnish to any Holder upon written request and without charge a copy of the Indenture. Requests may be made to: 

If to the Company: 

R. R. Donnelley & Sons Company 

35 West Wacker Drive 

Chicago, IL 60601 

Attention: General Counsel 

Fax: (312) 326-8594 

With a copy to: 

Skadden, Arps, Slate, Meagher & Flom LLP 

One Manhattan West 

New York, NY 10001 

Attention: Shilpi Gupta, Esq. and Michael J. Zeidel, Esq. 

Fax: (917) 777-3259 

  
 A-9 

 ASSIGNMENT 

I or we assign and transfer this Note to: 
  

 
 (Insert assignee’s social security
or tax I.D. number) 
  
  

(Print or type name, address and zip code of assignee) 

and irrevocably appoint: 
 Agent to transfer this Note on the
books of the Company. The Agent may substitute another to act for him. 
  

									
	Date:	 	  
	 		 	Your Signature:	 	  

		 		 		 		 	(Sign exactly as your name appears on the other side of this Note)
		
	Signature Guarantee:
                                         
                   	 	

 SIGNATURE GUARANTEE 

Signatures must be guaranteed by an “eligible guarantor institution” meeting the requirements of the Registrar, which requirements include
membership or participation in the Security Transfer Agent Medallion Program (“STAMP”) or such other “signature guarantee program” as may be determined by the Registrar in addition to, or in substitution for, STAMP, all in
accordance with the Securities Exchange Act of 1934, as amended. 

  
 A-10 

 OPTION OF HOLDER TO ELECT PURCHASE 

If you wish to have this Note purchased by the Company pursuant to Section 4.1 of the First Supplemental Indenture, check the box:
[    ]. 
 If you wish to have a portion of this Note purchased by the Company pursuant to Section 4.1 of the First
Supplemental Indenture, state the amount (in principal amount) below: 
 $_______________ 

Date:
                             

Your Signature:
                                         
    
 (Sign exactly as your name appears on the other side of this Note) 

Signature
Guarantee:                                     

Signatures must be guaranteed by an “eligible guarantor institution” meeting the requirements of the Registrar , which requirements
include membership or participation in the Security Transfer Agent Medallion Program (“STAMP”) or such other “signature guarantee program” as may be determined by the Registrar in addition to, or in substitution for,
STAMP, all in accordance with the Securities Exchange Act of 1934, as amended. 

  
 A-11 

 SCHEDULE OF INCREASES OR DECREASES IN GLOBAL NOTE* 

The following increases or decreases in this Global Note have been made: 

 

									
	 Date of

Exchange
	  	 Amount of

decreases in
 Principal

Amount of this Global Note
	  	 Amount of

increases in
 Principal

Amount of this
 Global Note
	  	 Principal amount

of this Global
 Note following

such decreases
 or increases
	  	 Signature of

authorized
 signatory of

Trustee or Notes

Custodian

		  		  		  		  	

  

	*	 This Schedule should be included only if the Note is issued in global form. 

  
 A-12EX-4.4

 Exhibit 4.4 

Execution Version 
  

 
 R.R. DONNELLEY & SONS
COMPANY 
 and 

WELLS FARGO BANK, NATIONAL ASSOCIATION, as Trustee 
  

 
 ELEVENTH
SUPPLEMENTAL INDENTURE 
 Dated as of June 18, 2020 

to 
 Indenture dated as
of January 3, 2007 
  
  

61⁄2% Notes due 2023 

 
  

 TABLE OF CONTENTS 

 

							
	 	  	 	 
		 	Article I	  			
			
		 	DEFINITIONS	  			
			
	 Section 1.1
	 	 Generally
	  	 	4	 
			
		 	Article II	  			
			
		 	AMENDMENTS	  			
	 Section 2.1
	 	 Certain Amendments to the Indenture
	  	 	4	 
			
		 	Article III	  			
			
		 	MISCELLANEOUS PROVISIONS	  			
	 Section 3.1
	 	 Ratification of Indenture
	  	 	5	 
	 Section 3.2
	 	 Trustee Not Responsible for Recitals
	  	 	5	 
	 Section 3.3
	 	 Table of Contents, Headings, etc.
	  	 	5	 
	 Section 3.4
	 	 Counterpart Originals
	  	 	5	 
	 Section 3.5
	 	 Governing Law; Jury Trial Waiver
	  	 	6	 

  
 2 

 THIS ELEVENTH SUPPLEMENTAL INDENTURE, dated as of June 18, 2020 (the “Eleventh
Supplemental Indenture”), between R.R. Donnelley & Sons Company, a Delaware corporation, as issuer (the “Company”), and Wells Fargo Bank, National Association, a national banking association, as trustee (the
“Trustee”). 
 RECITALS: 

WHEREAS, the Company has executed and delivered to the Trustee an Indenture, dated as of January 3, 2007 (the “Base
Indenture” and, together with the Ninth Supplemental Indenture (as defined below), the “Indenture”), providing for the issuance by the Company from time to time of its unsecured senior debentures, notes or other evidences
of indebtedness to be issued in one or more series unlimited as to principal amount (the “Securities”); 
 WHEREAS, the
Company has executed and delivered to the Trustee a Ninth Supplemental Indenture, dated as of November 12, 2013 (the “Ninth Supplemental Indenture”) to the Base Indenture governing the
61⁄2% Notes due 2023 (the “Notes”); 

WHEREAS, pursuant to the terms of a registration statement on Form S-4, initially filed by the Company
with the Securities and Exchange Commission on May 19, 2020, the Company offered to exchange validly tendered Notes and certain of its other outstanding debt securities for its new 8.250% senior notes due 2027 and solicited consents to certain
amendments to the Indenture with respect to the Notes and other Securities as set forth herein; 
 WHEREAS, Section 8.02 of the Base
Indenture provides that the Company and the Trustee may amend certain provisions of the Indenture or the Notes with the consent of the holders of a majority in aggregate principal amount of the Notes then outstanding (excluding any Notes owned by
the Company or any of its Affiliates), and such consent has been received by the Company; 
 WHEREAS, the Company desires the Trustee to
join with it in the execution and delivery of this Eleventh Supplemental Indenture, and in accordance with Sections 8.02, 8.06 and 10.04 of the Base Indenture, the Company has (i) duly adopted and delivered to the Trustee, resolutions of its
Board of Directors authorizing the execution and delivery of this Eleventh Supplemental Indenture, (ii) delivered to the Trustee evidence reasonably satisfactory to the Trustee that Holders of a majority in aggregate principal amount of the
Notes outstanding have given and, as of the date hereof, have not withdrawn their consents to the amendments set forth in this Eleventh Supplemental Indenture, and (iii) delivered to the Trustee an Officers’ Certificate and an Opinion of
Counsel stating that the execution of this Eleventh Supplemental Indenture is permitted by the Indenture and that all conditions precedent to its execution have been complied with, and the Indenture and this Eleventh Supplemental Indenture are valid
and binding obligations of the Company and are enforceable in accordance with their terms; 

  
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 WHEREAS, all things necessary to make this Eleventh Supplemental Indenture a valid agreement
of the Company and the Trustee, in accordance with its terms, and a valid amendment of, and supplement to, the Indenture have been done; 

NOW, THEREFORE, in consideration of the foregoing and for other good and valuable consideration, the receipt and sufficiency of which is
hereby acknowledged, the Company covenants and agrees with the Trustee, for the equal and ratable benefit of the Holders, that the Indenture is supplemented and amended, to the extent expressed herein, as follows: 

ARTICLE I 

DEFINITIONS 

Section 1.1    Generally. 

(a)    Capitalized terms used herein and not otherwise defined herein shall have the respective meanings ascribed thereto
in the Base Indenture. 
 (b)    The rules of interpretation set forth in the Base Indenture shall be applied hereto as
if set forth in full herein. 
 ARTICLE II 

AMENDMENTS 

Section 2.1    Certain Amendments to the Indenture. Solely with respect to the Notes, the Indenture is hereby
amended as follows: 
 (a)    each of Section 4.06 (Restrictions on Secured Debt), Section 4.07 (Restrictions
on Sale and Lease-Back Transactions), Section 4.08 (Reports to Holders), Section 4.09 (Statement by Officers as to Default), clause (a) of Section 5.01 (Consolidation, Merger and Sale of Assets), and clauses (d) and (e) of
Section 9.02 (Conditions to Defeasance) in the Base Indenture is hereby deleted in its entirety and replaced with “[Intentionally Omitted]”; 

(b)    the failure to comply with the terms of any of the provisions set forth in clause (a) above shall no longer
constitute a Default or an Event of Default under the Indenture and shall no longer have any other consequence under the Indenture; 

(c)    each of clauses (3), (4) and (5) of Section 6.01 (Events of Default) in the Base Indenture is hereby
deleted in its entirety and replaced with “[Intentionally Omitted]” and the occurrence of the events described in such clauses (3), (4) and (5) shall no longer constitute Events of Default; 

(d)    all definitions set forth in Section 1.01 of the Base Indenture that relate to defined terms used solely in
sections deleted by this Eleventh Supplemental Indenture are hereby deleted in their entirety; 

  
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 (e)    all references to Sections of the Indenture amended by this
Eleventh Supplemental Indenture shall mean such Section as amended by this Eleventh Supplemental Indenture; 

(f)    all references to Sections of the Indenture deleted pursuant to this Eleventh Supplemental Indenture are hereby
deleted in their entirety in the Indenture; and 
 (g)    all references to or descriptions of Sections of the Indenture
deleted pursuant to this Eleventh Supplemental Indenture are hereby deleted in their entirety from the Notes. 
 ARTICLE III 

MISCELLANEOUS PROVISIONS 

Section 3.1    Ratification of Indenture. The Indenture, as supplemented by this Eleventh Supplemental
Indenture, is in all respects ratified and confirmed, and this Eleventh Supplemental Indenture shall be deemed part of the Indenture in the manner and to the extent herein and therein provided. 

Section 3.2    Trustee Not Responsible for Recitals. The recitals contained herein and in the Notes shall be
taken as the statements of the Company, and the Trustee assumes no responsibility for the correctness of the same. The Trustee makes no representations as to and shall not be responsible for the validity or sufficiency of this Eleventh Supplemental
Indenture or of the Notes. The Trustee makes no representations as to and shall not be responsible for the Company’s 8.250% senior notes due 2027, the Company’s registration statement on Form S-4 and
the prospectus, initially filed by the Company with the Securities and Exchange Commission on May 19, 2020 or any amendment or supplement thereto, the solicitation of consents and the consents of the Holders of the Notes. In entering into this
Eleventh Supplemental Indenture, the Trustee shall be entitled to the benefit of every provision of the Indenture relating to the conduct or affecting the liability of or affording protection to the Trustee, whether or not elsewhere herein so
provided. The Company hereby confirms to the Trustee that this Eleventh Supplemental Indenture has not resulted in a material modification of the Notes for Foreign Account Tax Compliance Act (“FATCA”) purposes. The Trustee shall assume
that no material modification for FATCA purposes has occurred regarding the Notes, unless the Trustee receives written notice of such modification from the Company. 

Section 3.3    Table of Contents, Headings, etc. The table of contents and headings of the Articles and
Sections of this Eleventh Supplemental Indenture have been inserted for convenience of reference only, are not to be considered a part hereof and shall in no way modify or restrict any of the terms or provisions hereof. 

Section 3.4    Counterpart Originals. The parties may sign any number of copies of this Eleventh Supplemental
Indenture. Each signed copy shall be an original, but all of them together represent the same agreement. The exchange of copies of this Eleventh Supplemental Indenture and of signature pages by facsimile or PDF transmission shall constitute
effective execution and delivery of this Eleventh Supplemental Indenture as to the parties hereto and may be used in lieu of the original Eleventh Supplemental Indenture for all purposes. Signatures of the parties hereto transmitted by facsimile or
PDF shall be deemed to be their original signatures for all purposes. 

  
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 Section 3.5    Governing Law; Jury Trial Waiver. THIS
ELEVENTH SUPPLEMENTAL INDENTURE AND THE NOTES SHALL BE GOVERNED BY AND CONSTRUED IN ACCORDANCE WITH THE LAWS OF THE STATE OF NEW YORK. EACH OF THE COMPANY AND THE TRUSTEE HEREBY IRREVOCABLY WAIVES, TO THE FULLEST EXTENT PERMITTED BY APPLICABLE LAW,
ANY AND ALL RIGHT TO A TRIAL BY JURY IN ANY LEGAL PROCEEDING ARISING OUT OF OR RELATING TO THIS ELEVENTH SUPPLEMENTAL INDENTURE OR THE TRANSACTIONS CONTEMPLATED HEREBY. 

[Signature Pages Follow] 

  
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 IN WITNESS WHEREOF, the parties have caused this Eleventh Supplemental Indenture to be duly
executed all as of the date and year first written above. 
  

					
	R.R. DONNELLEY & SONS COMPANY
		
	By:	 	/s/ Terry D. Peterson
		 	Name: 	 	Terry D. Peterson
		 	 Title: 
	 	 Executive Vice President and

Chief Financial Officer

 [Eleventh Supplemental Indenture] 

 
			
	WELLS FARGO BANK, NATIONAL ASSOCIATION, as Trustee
		
	By:	 	/s/ Gregory S. Clarke
		 	Name: Gregory S. Clarke
		 	Title:   Vice President

 [Eleventh Supplemental Indenture]

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