Company: OSBC
Filing Date: 2025-05-06
Form Type: S-4/A
Source: 0001104659-25-045103
Chunk: 28

Company: OLD SECOND BANCORP INC
Filing Date: 2025-05-06
Form: S-4/A
Chunk 28
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 Date), or if the breach cannot be cured in such time;

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by Bancorp Financial, if Old Second breaches or is in breach of any of its representations, warranties, covenants, or agreements under the merger agreement, and such breach would, individually or in the aggregate, prevent the satisfaction of Bancorp Financial’s closing conditions, and is not cured within 30 days after written notice (or such shorter period remaining before the Termination Date), or if the breach cannot be cured in such time;

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by Old Second, at any time prior to the Bancorp Financial stockholder vote, if (i) Bancorp Financial has materially breached its non-solicitation and stockholder meeting obligations under the merger agreement, or (ii) Bancorp Financial’s board of directors fails to make its recommendation to the Bancorp Financial stockholders to adopt the merger agreement or withholds, withdraws, qualifies, or modifies its recommendation that stockholders approve the merger, fails to publicly reaffirm that recommendation upon request, or recommends a competing acquisition proposal; and

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by Bancorp Financial, if its board of directors determines, in accordance with its fiduciary duties and after compliance with its obligations under the merger agreement, to enter into a definitive agreement for a superior proposal, provided that Bancorp Financial is not in breach of its non-solicitation and stockholder meeting obligations under the merger agreement.

#### Termination Fee (page 74)
If the merger agreement is terminated under certain circumstances, including circumstances involving alternative acquisition proposals and changes in the recommendation of the Bancorp Financial board of directors, Bancorp Financial may be required to pay to Old Second a termination fee equal to $8,500,000. This termination fee could discourage other companies from seeking to acquire or merge with Bancorp Financial. For more information, see “The Merger Agreement — Effect of Termination” on page 74.

### Bancorp Financial Stockholders’ Appraisal Rights (page 88)
Bancorp Financial stockholders may be entitled to exercise appraisal rights in connection with the merger under Section 262 of the DGCL. If these rights are properly exercised and all procedural requirements

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are met, such stockholders will be entitled to receive payment in cash for the “fair value” of their shares of Bancorp Financial common stock, as determined by the Delaware Court of Chancery, instead of receiving the merger consideration. The “fair value” determined in an appraisal proceeding could be more than, less