Company: OSBC
Filing Date: 2025-05-06
Form Type: S-4/A
Source: 0001104659-25-045103
Chunk: 29

Company: OLD SECOND BANCORP INC
Filing Date: 2025-05-06
Form: S-4/A
Chunk 29
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 than, or the same as the value of the merger consideration. See “Bancorp Financial Stockholders’ Appraisal Rights” beginning on page 88.

A copy of Section 262 of the DGCL is attached as Annex C to this proxy statement/prospectus. You should read the statute carefully and consult with your legal counsel if you are considering exercising appraisal rights.

Comparison of Rights of Bancorp Financial Stockholders and Old Second Stockholders (page 94)

Following the merger, the rights of Bancorp Financial stockholders who become Old Second stockholders in the merger will remain governed by the laws of the State of Delaware but will no longer be governed by Bancorp Financial’s certificate of incorporation and bylaws, and instead will be governed by Old Second’s certificate of incorporation and bylaws. For more information, see “Comparison of Rights of Bancorp Financial Stockholders and Old Second Stockholders” beginning on page 94.

#### Risk Factors (page 19)
You should consider all the information contained in or incorporated by reference into this proxy statement/prospectus in deciding how to vote for the proposals presented in the proxy statement/prospectus. In particular, you should consider the factors described under “Risk Factors” beginning on page 19.

#### Accounting Treatment of the Merger (page 61)
For accounting and financial reporting purposes, the merger will be accounted for under the acquisition method of accounting for business combinations in accordance with accounting principles generally accepted in the United States of America, which we refer to as “GAAP.”

Material U.S. Federal Income Tax Consequences of the Merger (page 76)

The merger will qualify as a reorganization under Section 368(a) of the Internal Revenue Code of 1986, as amended, which we refer to as the “Code,” and it is a condition to the respective obligations of Old Second and Bancorp Financial to complete the merger that each receives a tax opinion to that effect. Therefore, for U.S. federal income tax purposes, “U.S. holders” (as defined in the section of this proxy statement/prospectus titled “Material U.S. Federal Income Tax Consequences of the Merger”) of Bancorp Financial common stock will recognize gain, but not loss, for U.S. federal income tax purposes in an amount equal to the lesser of (a) the amount of cash received (other than cash received in lieu of a fractional share of Old Second common stock) and (b) the excess, if any, of (i) the sum of the amount