Additional Proxy Soliciting Materials (Form DEFA14A)

UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

Washington, D.C. 20549

SCHEDULE 14A

(RULE 14a-101)

INFORMATION REQUIRED IN STATEMENT

SCHEDULE 14A INFORMATION

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Ryder System, Inc.

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(Name of Person(s) Filing Proxy Statement, if Other Than the Registrant)

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Important Message to Employee Shareholders - VOTE YOUR RYDER SHARES!

If you are a Ryder shareholder, I encourage you to vote your Ryder shares in advance of our 2026 Annual Meeting of Shareholders. Your vote helps ensure that shareholder views are represented on important governance matters.

As in the past, we ask that you vote in line with the Board's recommendations:

•"FOR" each of the director nominees in Proposal 1

•"FOR" Proposals 2 and 3 (ratification of our independent auditor and Say-On-Pay vote)

•"AGAINST" Proposal 4 (shareholder proposal requiring independent board chair)

Your vote is important because our Board opposes Proposal 4, which would require that the Chair of the Board be an independent director. As you may recall, we received nearly identical proposals in 2019 and 2023, and in both cases most of our shareholders voted AGAINST them. Our Board continues to believe this proposal is unnecessary and not in the interests of our shareholders. For the Board's full statement regarding this year's proposals, please refer to our 2026 Proxy Statement.

Please submit your vote by:

•April 28, 2026, for shares held through a plan, including through your 401(k), the Employee Stock Purchase Plan or through Ryder's Equity and Incentive Compensation Plan

•April 30, 2026, for shares held directly

Accessing Proxy Materials & Voting Instructions:

To vote your shares, you'll need a 16-digit control number. You should have received an e-mail with your control number and voting instructions from the institutions where you hold your shares - such as Morgan Stanley, Fidelity or another plan administrator or brokerage firm - or from [email protected].

If you own shares through multiple accounts, you should have received separate e-mails from each account. If you do not see the e-mail in your inbox, junk or spam folders, please contact a customer representative at the institution where you hold your shares.

Thank you for your continued support,

John J. Diez

Chief Executive Officer