Company: OSBC
Filing Date: 2025-04-23
Form Type: S-4
Source: 0001104659-25-037832
Chunk: 16

Company: OLD SECOND BANCORP INC
Filing Date: 2025-04-23
Form: S-4
Chunk 16
---
 of the Delaware General Corporation Law, which we refer to as the “DGCL,” be entitled to receive cash in the amount of the “fair value” of their shares of Bancorp Financial common stock instead of the merger consideration. If the stockholder and the surviving corporation do not agree on the fair value, it will be determined by the Delaware Court of Chancery. This “fair value” could be equal to, greater than, or less than the merger consideration. See “Bancorp Financial Stockholders’ Appraisal Rights” on page 88. A copy of Section 262 of the DGCL is attached as Annex C to this proxy statement/prospectus.

**Q: Are Old Second stockholders entitled to appraisal rights?**

A:

No, under the DGCL, which is the law under which Old Second is incorporated, the holders of Old Second common stock will not be entitled to any appraisal rights in connection with the merger.

Q:

What are the material U.S. federal income tax consequences of the merger to U.S. holders of Bancorp Financial common stock?

A:

The merger will qualify for U.S. federal income tax purposes as a “reorganization” within the meaning of 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 an opinion from its tax advisor or counsel to that effect. Therefore, “U.S.

<div align='center'>5</div>

TABLE OF CONTENTS

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 of such cash and the fair market value of the Old Second common stock received in the merger, over (ii) the U.S. holder’s adjusted tax basis in the shares of Bancorp Financial common stock surrendered in the merger. With respect to any cash received in lieu of a fractional share of Old Second common stock, a U.S. holder will recognize gain or loss measured by the difference between the amount of