Company: OSBC
Filing Date: 2025-05-06
Form Type: S-4/A
Source: 0001104659-25-045103
Chunk: 324

Company: OLD SECOND BANCORP INC
Filing Date: 2025-05-06
Form: S-4/A
Chunk 324
---
 or pertaining to, the fact that such person is or was a director or officer of Company or a Company Subsidiary and pertaining to matters, acts or omissions existing or occurring at or prior to the Effective Time (including matters, acts or omissions occurring in connection with the approval of this Agreement and the transactions contemplated by this Agreement) (each a “ Claim ”), whether asserted or claimed prior to, at or after the Effective Time, to the fullest extent permitted under the Company Certificate of Incorporation and Company Bylaws as in effect as of the date of this Agreement (subject to applicable Law), including provisions relating to advances of expenses incurred in the defense of any Litigation; provided, that the Indemnified Party to whom expenses are advanced provides a written undertaking to repay such advances if it is ultimately determined that such Indemnified Party is not entitled to indemnification.

(b) The Surviving Entity shall use its reasonable best efforts (and Company shall cooperate prior to the Effective Time in these efforts) to maintain in effect for a period of six (6) years after the Effective Time Company’s existing directors’ and officers’ liability insurance policy (provided that the Surviving Entity may substitute therefor (i) policies of at least the same coverage and amounts containing terms and conditions which are substantially no less advantageous to the insured, or (ii) with the consent of Company given prior to the Effective Time, any other policy) with respect to claims arising from facts or events which occurred prior to the Effective Time; provided, that the Surviving Entity shall not be obligated to make aggregate premium payments for such six (6) year period in respect of such policy (or coverage replacing such policy) which exceed, for the portion related to Company’s directors and officers, three hundred percent 300% of the annual premium payments currently paid on Company’s current policy in effect as of the date of this Agreement (the “ Maximum Amount ”). If the amount

<div align='center'>A-46</div>

TABLE OF CONTENTS

of the premiums necessary to maintain or procure such insurance coverage exceeds the Maximum Amount, the Surviving Entity shall use its reasonable best efforts to maintain the most advantageous policies of directors’ and officers’ liability insurance obtainable for a premium equal to the Maximum Amount. In lieu of the foregoing, Buyer, or Company in consultation with Buyer, may obtain on or prior to the Effective Time, a six (6) year “tail” prepaid policy providing equivalent coverage to that described in this Section 7.8(b