Company: OSBC
Filing Date: 2025-04-23
Form Type: S-4
Source: 0001104659-25-037832
Chunk: 13

Company: OLD SECOND BANCORP INC
Filing Date: 2025-04-23
Form: S-4
Chunk 13
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 nominee how to vote with respect to the adjournment proposal, you will be deemed not to be present with respect to the proposal, and it will have no effect on the proposal.

**Q: What are the conditions to complete the merger?**

**A:

The obligations of Old Second and Bancorp Financial to complete the merger are subject to the satisfaction or waiver of certain closing conditions set forth in the merger agreement. These conditions include the receipt of required regulatory approvals and the expiration of all applicable statutory waiting periods, the receipt of tax opinions, the approval of each of the merger proposal and the stockholders agreement amendment proposal by Bancorp Financial stockholders. For more information, see “The Merger Agreement — Conditions to Complete the Merger” beginning on page 72.

Q:**

#### When will the merger be completed?
A:

We will complete the merger when all of the conditions to completion contained in the merger agreement are satisfied or waived, including the receipt of required regulatory approvals and the expiration of all statutory waiting periods and approval by Bancorp Financial stockholders of the merger proposal and the stockholders agreement amendment proposal. While we expect the merger to

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be completed in the third quarter of 2025, because fulfillment of some of the conditions to completion of the merger are not entirely within our control, we cannot assure you of the actual timing.

Q:

How does the Bancorp Financial board of directors recommend that I vote?

A:

The Bancorp Financial board of directors has unanimously determined that the merger agreement, the merger and the other transactions contemplated by the merger agreement, are advisable, fair to and in the best interests of Bancorp Financial and its stockholders and unanimously recommends that Bancorp Financial stockholders vote “FOR” the merger proposal, “FOR” the stockholders agreement amendment proposal, and “FOR” the adjournment proposal.

#### Q:   What do I need to do now?
**A:

After carefully reading and considering the information contained in or incorporated by reference into this proxy statement/prospectus, including its annexes, please vote your shares as soon as possible so that your shares will be represented at the Bancorp Financial special meeting. Please follow the instructions set forth herein or on the enclosed proxy card or on the voting instruction form provided by your bank, broker or other nominee if your shares are held in “street name” by a bank, broker or other nominee.

Q:

If my shares are held in “street name” by a bank,