Each holder of our Common Stock will be entitled to cast one vote per share for or against each of the director nominees.

Unless there are director nominees other than those nominated by the Board of Directors, a director nominee will be elected as a director if the votes cast for his or her election exceed votes cast against his or her election. In this case, any director nominee who does not receive a majority of votes cast “for”“FOR” his or her election would be required to tender his or her resignation following the failure to receive the required vote. For the 2024 Annual Meeting, the number of director nominees equals the number of directors to be elected, so this voting standard will apply. Pursuant to the Company’s By-Laws,By-Laws, if the Secretary of the Company determineshad determined that the number of director nominees exceedsexceeded the number of directors to be elected as of the date seven days prior to the scheduled mail date of thethis proxy statement, a plurality voting standard willwould apply and a director nominee receiving a plurality of votes cast willwould be elected as a director. Brokers do not have discretionary authority to vote shares on this proposal without direction from the beneficial owner. For the purpose of electing directors, broker non-votesnon-votes and abstentions are not treated as a vote cast affirmatively or negatively, and therefore will not affect the outcome of the election of directors. Both abstentions and broker non-votes are counted for purposes of determining the presence of a quorum. If your properly executed proxy does not specify how you want your shares voted, the shares represented by your proxy will be voted “FOR” each of the director nominees.

Our stockholders will vote on the approval of the advisory resolution regarding the compensation of our named executive officers. Approval of this proposal requires the affirmative vote of the majority of the shares voted on this proposal at the 20222024 Annual Meeting. Brokers do not have discretionary authority to vote shares on this proposal without direction from the beneficial owner. Broker non-votes will not be counted. Abstentions, which will be

You may revoke or change a previously delivered proxy at any time prior to its exercise at the 20222024 Annual Meeting by the following methods:

You may vote by attending the 20222024 Annual Meeting which is being held virtually and voting at the virtual meeting, or you may vote by submitting a proxy. If you are the record holder of your stock, you may vote by submittingsubmit your proxy via the Internet, by telephone or through the mail.

To vote via the Internet, follow the instructions on the Notice or go to the Internet address stated on your proxy card. To vote by telephone, call the number on your proxy card. If you receive only the Notice, you may follow the procedures outlined in the Notice, which contains instructions on how to vote via the Internet or by telephone or receive a paper proxy card to vote by mail. Internet and telephone voting for Common Stock are available through 11:59 p.m. Eastern Time on May 25, 2022.

As an alternative to voting by telephone or via the Internet, you may vote by mail. If you receive only the Notice, you may follow the procedures outlined in the Notice to request a paper proxy card to submit your vote by mail. If you receive a paper copy of the proxy materials and wish to vote by mail, simply mark your proxy card, date and sign it, and return it in the postage-prepaidpostage-prepaid envelope. Proxy cards sent by mail, if received in time for voting and not revoked, will be voted at the Annual Meeting according to the instructions on the proxy cards. If no instructions are indicated, the shares represented by the proxy will be voted as set forth above under “Record Date; Voting Rights; and Outstanding Shares.”

If you hold your shares of our Common Stock in street name, you will receive the Notice from your broker, bank, or other nominee that includes instructions on how to vote your shares. Your broker, bank, or other nominee will allow you to deliver your voting instructions via the Internet and may also permit you to submit your voting instructions by telephone. In addition, you may request paper copies of this proxy statement and proxy card by following the instructions on the Notice provided by your broker, bank, or other nominee.

Stockholders who submit a proxy via the Internet should be aware that they may incur costs to access the Internet, such as usage charges from telephone companies or Internet service providers and that these costs must be borne by such stockholders. Stockholders who submit a proxy via the Internet or by telephone need not return a proxy card or the form forwarded by your broker, bank, or other nominee by mail.

The Annual Meeting will begin promptly at 8:30 a.m., Central Time. We encourage you to access the virtual meeting platform prior to the start time leaving ample time for check-in.check-in. Please follow the registration instructions as outlined in this proxy statement.

Questions pertinent to meeting matters will be answered during the 20222024 Annual Meeting. The 20222024 Annual Meeting is not to be used as a forum to present personal matters, or general economic, political, or other views that are not directly related to the business of Stewart and the matters properly before the 20222024 Annual Meeting, and therefore questions on such matters will not be answered.

If you are a registered stockholder (i.e., you hold your shares through our transfer agent, Computershare), you do not need to register to attend the 20222024 Annual Meeting virtually on the Internet. Please follow the instructions on the Notice or proxy card that you received.

If you hold your shares through an intermediary, such as a bank or broker, you must register in advance to attend the 20222024 Annual Meeting virtually on the Internet.

To register to attend the 20222024 Annual Meeting online you must submit proof of your proxy power (legal proxy) reflecting your Stewart holdings along with your name and email address to Computershare. Requests for registration must be labeled as “Legal Proxy” and be received no later than 5:00 p.m., Eastern Time, on May 23, 2022.

You will receive a confirmation of your registration by email after we receive your registration materials.

We are currently managed by a Board of Directors comprised of nineten members, the majority of whom are “independent” within the meaning of the listing standards of the NYSE. Assuming the election of the 20222024 director slate set proposed by the Company and described above, these independent directors are: Thomas G. Apel, C. Allen Bradley, Jr., William S. Corey, Jr., Robert L. Clarke, C. Allen Bradley, Jr., Deborah J. Matz, Karen R. Pallotta, Manolo Sánchez, and Manuel Sánchez.Helen Vaid. The Board of Directors has determined that none of these directors has any material relationship with us or our management that would impair the independence of their judgment in carrying out their responsibilities to us. In making this determination, the Board of Directors considers any transaction, or series of similar transactions, or any currently proposed transaction, or series of similar transactions, between us or any of our subsidiaries and a director to be material if the amount involved exceeds $120,000, exclusive of directors’ fees, in any of our last three fiscal years.

The roles of Chairman of the Board of Directors and CEO are separate, and each role is held by a different individual. The Chairman of the Board of Directors is elected by the Board of Directors following the annual meeting of stockholders. As discussed below, the Chairman of the Board presides over the regular and any special meetings of our non-managementnon-management directors. Our non-managementnon-management directors meet after each regularly scheduled Board meeting.

All of our directors shall be elected at the 20222024 Annual Meeting and hold office until the next annual election of directors or until his or her successor shall be chosen and shall be qualified, or until his or her death or the effective date of his or her resignation or removal for cause. Currently, the act of the majority of a quorum of the directors shall be the act of the Board of Directors, except as may be otherwise specifically provided by statute, the Certificate of Incorporation, or the By-Laws.

Each of our directors is an individual of high character and integrity, with an inquiring mind, and works well with others. Each director nominee brings a unique background and set of skills to the Board, giving the Board of Directors, as a whole, competence and experience in a wide variety of areas, including insurance, real estate, technology, strategic planning, corporate governance, executive management, accounting, finance,

The Board of Directors has ultimate responsibility for protecting value for all stakeholders. Among other things, the Board of Directors is responsible for understanding the risks to which we are exposed, approving management’s strategy to manage these risks, and monitoring and measuring management’s performance in implementing the strategy. The Board of Directors works with its committees and management to effectively implement its risk oversight role.

For 2022,2024, the Board of Directors will have the following committees (the “Committees”): an Audit Committee, a Nominating and Corporate Governance Committee, and a Compensation Committee.

The Audit Committee has sole authority to appoint or replace our independent registered accountants. The Audit Committee has the authority to engage independent counsel and other advisors as it determines necessary to carry out its duties. For a complete list of the Audit Committee’s responsibilities, please see the Audit Committee charter adopted by our Board of Directors, which is available on our website at

Persons wishing to communicate with the Audit Committee may do so by writing in care of the Chair, Audit Committee, Stewart Information Services Corporation, 1360 Post Oak Boulevard, Suite 100, Houston, Texas 77056.

Pursuant to our By-Laws,By-Laws, the Nominating and Corporate Governance Committee will accept and consider director nominations made by stockholders. To be considered for nomination at our 20232024 annual meeting of stockholders, stockholder nominations must be received by us no later than February 25, 2023,7, 2024, and no earlier than January 26, 2023. 8, 2024. In addition to satisfying the foregoing requirements under our By-Laws, to comply with the universal proxy rules, stockholders who intend to solicit proxies in support of director nominees other than our nominees must provide notice that sets forth the information required by Rule 14a-19 under the Exchange Act.

Persons wishing to submit the names of candidates for consideration by the Nominating and Corporate Governance Committee may submit such nominations in writing addressed to the Nominating and Corporate Governance Committee in care of the Secretary, Stewart Information Services Corporation, 1360 Post Oak Boulevard, Suite 100, Houston, Texas 77056. Any such submission should include the information required by our By-Laws, including the candidate’s name, credentials, contact information and consent to be considered as a candidate.

In addition, the Compensation Committee has the sole authority to retain and terminate any independent compensation consultant. The Compensation Committee is responsible for determining the independence of its advisors by taking into consideration all factors relevant to advisor independence, including the factors set forth in the NYSE Listed Company Manual. The Compensation Committee has authority to direct the work of the compensation consultants and establish the consultants’ fees. It may also obtain advice and assistance from other advisors it determines necessary for effective completion of its duties. The Company is required to fund (i) the Compensation Committee’s approved expenses for any independent advisors employed by the Compensation Committee, and (ii) any other reasonable expenses incurred by the Compensation Committee.

In an effort to more closely link our non-employeenon-employee directors’ financial interests with those of our stockholders, our Board established share ownership guidelines for our non-managementnon-management directors. Each director is required to own an amount of Common Stock equal to a multiple of five times the stock portion of the annual director retainer. Each director has five years from their initial election to acquire the required amount of Common Stock. Currently, five seven

During 2021,2023, the Compensation Committee members were Karen R. Pallotta (Chair), Thomas G. Apel, (Chair), William S. Corey and Karen R. Pallotta.Helen Vaid. None of the current or former members of the Compensation Committee is a former or current officer or employee of the Company or any of its subsidiaries. None of our executive officers currently serve, or has served during the last completed fiscal year, on the compensation committee or board of directors of any other entity that has one or more executive officers serving as a member of our Board of Directors or Compensation Committee. Please refer to “Certain Transactions” for information regarding Mr. Apel.

Our independentnon-management directors meet at regularly scheduled sessions without management.sessions. The Chairman of the Board presides at those sessions. Persons wishing to communicate with our non-managementnon-management directors may do so by writing in care of the Chair, Audit Committee, Stewart Information Services Corporation,

The following table sets forth the names and positions of our executive officers as of April 1, 2022:

The Company holds an advisory vote on executive compensation every year. An overwhelming majority (98.1%(98.5%) of the votes on our 2021 Say-on-Pay2023 Say-on-Pay proposal were cast in favor of the proposal, which was similar to our 20202022 result. The Committee interprets this continued strong level of support as affirmation of the overall structure of our executive compensation program and our approach to compensation decisions. As our business evolves, we are committed to the continuous improvement of our executive compensation program to ensure alignment with our strategic business priorities, to support our ESG initiatives, ability to attract, motivate and retain top executive talent, and stockholder interests.

Below we highlight our key executive compensation practices, both the practices we have implemented to drive performance, and the practices we have not implemented because we do not believe they would serve our stockholders’shareholders’ interests.

The Company’s executive compensation structure follows a “pay-for-performance”“pay-for-performance” philosophy by providing a meaningful relationship between the compensation earned by our executives, the overall success of our organization, and the returns generated to our stockholder.

Our executive compensation program is also intended to be market competitive. For 2021,2023, the Committee approved a “total‘‘total direct compensation opportunity”opportunity’’ for each executive officer consisting of base salary, target short-termshort-term incentive compensation, and target long-termlong-term incentive compensation. The intent is for total direct compensation to be competitive among the comparator group, specifically targeting the pay comparator group median. The Committee also considers historical and individual circumstances, including tenure, experience, individual performance, retention factors, and the availability of comparable data for each position.

The Committee believes the majority of executive officer compensation should be “at-risk,”“at-risk,’’ with the realized value heavily dependent upon the Company’s financial, operational, and stockholdershareholder return performance. We believe executive officers should be rewarded appropriately for their efforts when financial performance meets or exceeds established objectives. Likewise, incentive compensation may be reducedbelow target or eliminatednot be earned if performance does not meet established goals. Incentivegoals or thresholds. Additionally, we believe executive officers should also be evaluated on their leadership competencies and individual contributions and achievements on key non-financial company objectives that contribute to our vision of being the premier title services company. These beliefs form the foundation of our incentive compensation, which is designed to appropriately balance annual results and the Company’s sustained, multi-yearmulti-year success. Short-termShort-term awards are payable in cash, while long-termlong-term awards are equity-based.

We believe one of the pay philosophy,most important and primary objectives of our executive compensation program is to create a strong and meaningful relationship between the compensation earned by our executive officers and the long-term sustainable success of our Company continuedand shareholders. During 2023, in support of this objective, the Committee determined that the performance goals under the STIP set in the fourth quarter of 2022 did not appropriately reflect the increased risk that the business forecasts used to focus on ownership and ownership-minded behaviors, and on profitable growth for 2021. Asestablish 2023 performance goals could be materially inaccurate as a result of the Company’s inability to reasonably predict the timing, magnitude or direction of Federal Reserve monetary policy decisions and their resulting impact on the housing finance market. In response, the Committee widened the STIP performance ranges by lowering the threshold and increasing the maximum goals for our performance metrics. This resulted in 2021,threshold performance targets reflective of the Company continueddownside risk to growreal estate activity and more rigorous maximum performance targets to minimize the numberrisk of participants in its long-term incentive program (“LTIP”).excessive payouts. The Company also added atarget performance goal for each performance metric was not adjusted and the payout opportunities for each NEO were not modified. The Committee believed this approach would better align with our pay-for-performance philosophy by reducing the risk of inaccurate forecasts contributing to its LTIP based on Pre-Tax Margin.either excessive or overly punitive payouts. See the “Performance Based Restricted Stock Units”“2023 Performance Metrics, Goals, Results and Bonus Payouts” section for more information.

To provide our NEOs and other executive officers with compensation that is competitive, target pay levels are generally set at the median for the pay comparator group with an opportunity to earn compensation in excess of the median in return for exceeding performance goals.

The core principle of our executive compensation philosophy is to pay for performance. Accordingly, our executive officer compensation program is heavily weighted toward “at-risk”‘‘at-risk’’ variable compensation.

We have three elements of total direct compensation: base salary, short-termshort-term incentive, and long-termlong-term incentive. As illustrated in the charts below, in 2021,2023, 78% of target total direct compensation to Mr. Eppinger, our CEO, was variable and “at-risk”“at-risk”, while the average mix of other NEO target total direct compensation was 71%69% variable and “at-risk”“at-risk”.

When considering our compensation practices and pay levels, the Committee reviews the compensation practices and pay levels of a comparator group of companies to determine market levels. Since there are only four publicly held-held title insurance companies, and two of those are substantially larger than us,the Company, a pay comparator group was established by the Committee that reflects companies of comparable size that share a comparable labor market. The Committee periodically reviews the composition of this group to ensure that the companies in the group are relevant for comparative purposes and that the companies in the group have executive officer positions with similar scope and responsibilities.

To identify an appropriate comparison group, the Committee and its independent compensation consultant reviewed data for potential comparators relating to revenue including the role of agency revenue, market capitalization (generally 0.5x to 2.0x our size), market capitalization, and sector within the insurance industry. The Committee also considered business focus (such as title companies, mortgage insurance companies, property/casualty insurance companies, mortgage companies, reinsurance companies, and similar companies within the insurance sector) and the relevance of the company as a comparator based on a “comparator‘‘comparator of comparators”comparators’’ assessment, which includes comparator companies of the other publicly held-held title companies.

For 2021,2023, the Committee approved maintainingconsidered the sameCompany’s size relative to the companies in last year’s comparator group thatand approved changes designed to maintain companies of comparable size. American Equity Investment Life Holding Company, CNO Financial Group, and Hilltop Holdings were removed considering business focus, and Employers Holdings, Enstar Group, James River Group Holdings, Safety Insurance Group, and United Fire Group were all removed considering their relatively smaller revenue size. American National Insurance Company was establishedacquired in 2020 except for National General Holdings Corporation, which was acquiredMay 2022 and is no longer publicly traded. Cincinnati Financial Corporation, Rocket Companies, Erie Indemnity Company, Mr. Cooper Group, UWM Holdings Corporation, and PennyMac Financial Services were all added.