Company: OSBC
Filing Date: 2025-05-06
Form Type: S-4/A
Source: 0001104659-25-045103
Chunk: 123

Company: OLD SECOND BANCORP INC
Filing Date: 2025-05-06
Form: S-4/A
Chunk 123
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 among different blocks of shares of Bancorp Financial common stock for purposes of determining recognized gain and the tax bases and holding periods of the particular shares of Old Second common stock received in the merger.

#### Cash Received in Lieu of a Fractional Share
#### .

If a U.S. holder receives cash in the merger instead of a fractional share of Old Second common stock, the U.S. holder will be treated as having received such fractional share in the merger, and then as having sold such fractional share for cash. As a result, the U.S. holder will recognize gain or loss equal to the difference between the cash received and the U.S. holder’s adjusted tax basis in the shares of Bancorp Financial common stock surrendered allocable to that fractional share. This gain or loss generally will be long-term capital gain or loss if the holding period for those shares of Bancorp Financial common stock is more than one year as of the date of the merger, unless the receipt of cash has the effect of a distribution of a dividend under the provisions of the Code (as discussed above). The deductibility of capital losses is subject to limitations.

#### Medicare Tax on Net Investment Income.
An unearned income Medicare contribution tax of 3.8% could apply to some or all of the gain and any of the proceeds taxable as a dividend that a noncorporate U.S. holder recognizes in the merger, depending on the U.S. holder’s level of modified adjusted gross income (or adjusted gross income in the case of a trust or estate) and the other provisions of Section 1411 of the Code. The unearned income Medicare contribution tax applies to “net investment income” of a U.S. holder, which may include capital gains or dividends recognized by U.S. holders as a result of the merger. U.S. holders should consult their individual tax advisors regarding the potential applicability of the unearned income Medicare contribution tax.

#### Backup Withholding.
Backup withholding on any cash payments received at the applicable rate (currently at a rate of 24%) may, under certain circumstances, apply unless a U.S. holder (a) is a corporation or is within certain other exempt categories and, when required, demonstrates this fact, or (b) provides a correct taxpayer identification number, certifies as to no loss of exemption from backup withholding and otherwise complies with applicable requirements of the backup withholding rules. A U.S. holder who does not provide his, her or its correct taxpayer identification number may be subject to penalties imposed by the IRS. Any amounts withheld