Company: OSBC
Filing Date: 2025-04-18
Form Type: DEF 14A
Source: 0001558370-25-005000
Chunk: 107

Company: OLD SECOND BANCORP INC
Filing Date: 2025-04-18
Form: DEF 14A
Chunk 107
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 the contact information below.

If requested, we will also promptly deliver, upon oral or written request, a separate copy of the proxy statement and annual report to any stockholder residing at an address to which only one copy was mailed. Please address such requests to our Stockholder Relations Manager at the contact information below.

<div align='center'>Stockholder Relations Manager, Shirley Cantrell

Old Second Bancorp, Inc.

37 S. River St.

Aurora, Illinois 60507

Telephone: 630-906-2303

68</div>

GENERAL We will bear the cost of this proxy solicitation. Solicitation will be made primarily through the use of the mail, but our officers, directors or employees may solicit proxies personally, by telephone or through any other mode of communication, without additional remuneration to our officers, directors or employees for such activity. In addition, we will reimburse brokerage houses and other custodians, nominees or fiduciaries for their reasonable expenses in forwarding proxy materials to the beneficial owner of such shares. As of the date of this proxy statement, we do not know of any other matters to be brought before the annual meeting. However, if any other matters should properly come before the meeting, it is the intention of the persons named in the enclosed proxy to vote thereon in accordance with their best judgment.

| ​                              | ​                                               |
| ​                              | By order of the board of directors              |
| ​                              |                                                 |
| ​                              | James L. Eccher                                 
 Chairman, President and Chief Executive Officer |
| Aurora, IllinoisApril 18, 2025 | ​                                               |

69

<div align='center'>Appendix A

Marked Version of Certificate of Incorporation Showing Proposed Amendments

ARTICLE IV

AUTHORIZED STOCK</div>

A. The total number of shares of all classes of stock which the Corporation shall have authority to issue is60,300,000120,300,000shares, which are divided into two classes:

60,000,000120,000,000shares of common stock, with a par value of $1.00 per share; and

300,000 shares of preferred stock, with a par value of $1.00 per share.

<div align='center'>70

Appendix B

CERTIFICATE OF AMENDMENT

TO THE

RESTATED CERTIFICATE OF INCORPORATION

OF

OLD SECOND BANCORP, INC.

(Pursuant to 8 Del. C. Section 242)</div>

Old Second