UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

Washington, D.C. 20549

Schedule 14A

Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

(Amendment No. )

Filed by the Registrant x

Filed by a party other than the Registrant ¨

Check the appropriate box:

¨ Preliminary Proxy Statement

¨ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2))

¨ Definitive Proxy Statement

x Definitive Additional Materials

¨ Soliciting Material under § 240.14a-12

Stewart Information Services Corporation

(Name of Registrant as Specified In Its Charter)

(Name of Person(s) Filing Proxy Statement, if other than the Registrant)

Payment of Filing Fee (Check all boxes that apply):

x No fee required

¨ Fee paid previously with preliminary materials.

¨ Fee computed on table in exhibit required by Item 25(b) per Exchange Act Rules 14a- 6(i)(1) and 0-11

Step 1: Go to www.envisionreports.com/STC. Step 2: Click on Cast Your Vote or Request Materials. Step 3: Follow the instructions on the screen to log in. www.envisionreports.com/STC Online Go to www.envisionreports.com/STC or scan the QR code — login details are located in the shaded bar below. Stockholder Meeting Notice 03M3FD + + Important Notice Regarding the Availability of Proxy Materials for the Stewart Information Services Corporation Stockholder Meeting to be Held on May 26, 2022 Under Securities and Exchange Commission rules, you are receiving this notice that the proxy materials for the annual stockholders’ 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. We encourage you to access and review all of the important information contained in the proxy materials before voting. The Notice of Annual Meeting of Stockholders, Proxy Statement, and Annual Report on Form 10-K 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 May 16, 2022 to facilitate timely delivery. 2NOT 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.

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/STC. 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 Stewart Information Services Corporation” 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 May 16, 2022. Stewart Information Services Corporation’s Annual Meeting of Stockholders will be held on May 26, 2022 at 8:30 a.m. Central Time and will be completely virtual. You may access the meeting online, vote your shares electronically and submit your questions during the meeting by visiting www.meetnow.global/MF4ZDPF. You must use the 15-digit control number included on this Notice to join the meeting at the set date and time. Proposals to be voted on at the meeting are listed below along with the Board of Directors’ recommendations. The Board of Directors recommend a vote FOR all the nominees listed and FOR Proposals 2 and 4 and every 1 YEAR on Proposal 3. 1. Election of Directors: 01 Thomas G. Apel 02 C. Allen Bradley, Jr. 03 Robert L. Clarke 04 William S. Corey, Jr. 05 Frederick H. Eppinger, Jr. 06 Deborah J. Matz 07 Matthew W. Morris 08 Karen R. Pallotta 09 Manuel Sánchez 2. Approval of the compensation of Stewart Information Services Corporation’s named executive officers (Say-on-Pay). 3. Approval of the frequency of the vote on the compensation of Stewart Information Services Corporation’s named executive officers (Say-When-on-Pay). 4. Ratification of the appointment of KPMG LLP as Stewart Information Services Corporation’s independent auditors for 2022. Any other business that properly comes before 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. Stockholder Meeting Notice