Company: OSBC
Filing Date: 2025-05-08
Form Type: 424B3
Source: 0001104659-25-046065
Chunk: 122

Company: OLD SECOND BANCORP INC
Filing Date: 2025-05-08
Form: 424B3
Chunk 122
---
 a U.S. holder in the merger (including any fractional share of Old Second common stock deemed received and redeemed for cash, as discussed below) will include the holding period of the shares of Bancorp Financial common stock surrendered.

If a U.S. holder exchanges more than one “block” of shares of Bancorp Financial common stock (that is, groups of shares that the U.S. holder acquired at different times or at different prices), the U.S. holder must calculate gain, adjusted tax basis and holding period separately as to each block of shares. Any such U.S. holder should consult with his, her or its own tax advisors regarding the manner in which shares of Old Second common stock and cash received in the merger should be allocated 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