[DEFA14A] Midland States Bancorp, Inc. Additional Proxy Soliciting Materials

Step 1: Go to www.envisionreports.com/MSBI. Step 2: Click on Cast Your Vote or Request Materials. Step 3: Follow the instructions on the screen to log in. www.envisionreports.com/ABCcompany Online Go to www.envisionreports.com/MSBI or scan the QR code — login details are located in the shaded bar below. Shareholder Meeting Notice 045QAA Important Notice Regarding the Availability of Proxy Materials for the Midland States Bancorp, Inc. Shareholder Meeting to be Held on August 4, 2025 Under Securities and Exchange Commission rules, you are receiving this notice that the proxy materials for the annual shareholders’ meeting are available on the Internet. Follow the instructions below to view the materials and vote online or request a copy. The items to be voted on and location of the annual meeting are on the reverse side. Your vote is important! This communication presents only an overview of the more complete proxy materials that are available to you on the Internet or by mail. We encourage you to access and review all of the important information contained in the proxy materials before voting. The 2025 Proxy Statement and Annual Report on Form 10-K for the year ending December 31, 2024 are available at: Obtaining a Copy of the Proxy Materials – If you want to receive a copy of the proxy materials, you must request one. There is no charge to you for requesting a copy. Please make your request as instructed on the reverse side on or before July 28, 2025 to facilitate timely delivery. 2 N O T Easy Online Access — View your proxy materials and vote. When you go online, you can also help the environment by consenting to receive electronic delivery of future materials. Step 4: Make your selections as instructed on each screen for your delivery preferences. Step 5: Vote your shares. Votes submitted electronically must be received by August 1, 2025 at 11:59 PM, local time. MMMMMMMMMMMM MMMMMMMMM 000001MR A SAMPLE DESIGNATION (IF ANY) ADD 1 ADD 2 ADD 3 ADD 4 ADD 5 ADD 6 ENDORSEMENT_LINE______________ SACKPACK_____________ 1234 5678 9012 345 C 1234567890 C O Y MMMMMMM MSBI

Here’s how to order a copy of the proxy materials and select delivery preferences: Current and future delivery requests can be submitted using the options below. If you request an email copy, you will receive an email with a link to the current meeting materials. PLEASE NOTE: You must use the number in the shaded bar on the reverse side when requesting a copy of the proxy materials. — Internet – Go to www.envisionreports.com/MSBI. Click Cast Your Vote or Request Materials. — Phone – Call us free of charge at 1-866-641-4276. — Email – Send an email to investorvote@computershare.com with “Proxy Materials Midland States Bancorp, Inc.” in the subject line. Include your full name and address, plus the number located in the shaded bar on the reverse side, and state that you want a paper copy of the meeting materials. To facilitate timely delivery, all requests for a paper copy of proxy materials must be received by July 28, 2025. Midland States Bancorp, Inc.’s Annual Meeting of Shareholders will be held on August 4, 2025 at the Holiday Inn, located at 1301 Avenue of Mid-America, Effingham, Illinois 62401, at 5:30 p.m. CT. Proposals to be voted on at the meeting are listed below along with the Board of Directors’ recommendations. The Board of Directors recommends a vote FOR all nominees and FOR Proposals 2, 4 and 1 YEAR on Proposal 3. 1. To elect the three nominees named in the accompanying proxy statement to serve as Class III directors, each for a term expiring at the 2028 annual meeting of shareholders. 01 - R. Dean Bingham 02 - Jerry L. McDaniel 03 - Jeffrey M. McDonnell 2. To approve, on a non-binding, advisory basis, the compensation of certain executive officers, which we refer to as the “say-on-pay proposal.” 3. To approve, on a non-binding, advisory basis, the frequency with which shareholders will vote on future say-on-pay proposals, which we refer to as the “say-on-frequency proposal.” 4. To ratify the appointment of Crowe LLP as our independent registered public accounting firm for the year ending December 31, 2025; and 5. To transact such other business as may properly be brought before the meeting and any adjournments or postponements of the meeting. PLEASE NOTE – YOU CANNOT VOTE BY RETURNING THIS NOTICE. To vote your shares you must go online or request a paper copy of the proxy materials to receive a proxy card. If you wish to attend and vote at the meeting, please bring this notice with you. Shareholder Meeting Notice