RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS 2024 INVESTOR DAY June 13 | NYC Exhibit 99.2

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Welcome and Opening Remarks Calene Candela VP, Investor Relations 2

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Safe Harbor and Non-GAAP Financial Measures 3 Note Regarding Forward-looking Statements: Certain statements and information included in this news release are “forward-looking statements” under the Federal Private Securities Litigation Reform Act of 1995, including our expectations regarding: our forecast; outlook; long-term targets; market trends and economic environment, such as rental demand, utilization, economic growth, freight environment, used vehicle sales and rental, volumes in our omnichannel retail vertical, and total addressable market; the freight cycle, including timing and the impact of the freight cycle on our businesses; total and operating revenue, earnings per share, comparable earnings per share, adjusted ROE (ROE), earnings before income tax, net cash from operating activities from continuing operations, debt-to- equity, capital expenditures, operating cash flow, free cash flow, compound annual growth rate, and the causes of change; execution of our balanced growth strategy; the impact of inflationary pressures, such as inflationary cost recovery; expectations with respect to offerings, including ChoiceLease and RyderElectric+, amongst others; timing of OEM deliveries and vehicle production; our actions to increase returns and create long-term value; our ability to outperform prior cycles; expectations regarding long-term profitable growth and secular trends; expectations and benefits from strategic initiatives, including lease pricing and maintenance cost savings initiatives, our ability to leverage a multi-client network, and to deploy flexible operating structure; expectations regarding customer operations; expectations regarding used vehicle inventory and fleet size; our ability to redeploy rental vehicles and leverage our expanded retail used vehicle network; our ability to execute our enhanced asset management playbook; our ability to support organic growth, including growing our contractual lease, dedicated, and supply chain businesses at targeted returns; expectations regarding strategic investments and acquisitions, including the acquisitions of Cardinal Logistics and Impact Fulfillment Services and expected integration timeline and synergies; expectations regarding cross-border capabilities; expectations regarding Ryder technologies; and expectations regarding our ability to return capital to shareholders, including through share repurchases and dividends. Our forward-looking statements also include our estimates of the impact of residual value estimates on earnings and depreciation expense that is based in part on our current assessment of the residual values and useful lives of revenue-earning equipment based on multi-year trends and our outlook for the expected near- and long-term used vehicle market. A variety of factors, many of which are outside of our control, could cause residual value estimates to differ from actual used vehicle sales pricing, such as changes in supply and demand of used vehicles; volatility in market conditions; changes in vehicle technology; competitor pricing; regulatory requirements; driver shortages; customer requirements and preferences; and changes in underlying assumption factors. All of our forward-looking statements should be evaluated by considering the many risks and uncertainties inherent in our business that could cause actual results and events to differ materially from those in the forward-looking statements. Important factors that could cause such differences include: changes in general economic and financial conditions in the U.S. and worldwide; the ongoing supply chain and labor challenges and vehicle production constraints, including OEM delays; the effect of geopolitical events; our ability to adapt to changing market conditions, including lower than expected contractual sales, decreases in commercial rental demand or utilization, poor acceptance of rental pricing, declining market demand for or excess supply of used vehicles impacting current or estimated pricing, and our anticipated proportion of retail versus wholesale sales; declining customer demand for our services; higher than expected maintenance costs; lower than expected benefits from our cost-savings initiatives; our ability to effectively and efficiently integrate acquisitions into our business; lower than expected benefits from our sales, marketing, and new product initiatives; setbacks in the economic market or in our ability to retain profitable customer accounts; impact of changing laws and regulations; difficulty in obtaining adequate profit margins for our services; inability to maintain current pricing levels due to, for example, economic conditions, business interruptions, expenditures, labor disputes, and severe weather or other natural occurrences; competition from other service providers; changes in technology and new entrants; professional driver and technician shortages resulting in higher procurement costs and turnover rates; impact of supply chain disruptions; higher than expected bad debt reserves or write-offs; decrease in credit ratings; increased debt costs; adequacy of accounting estimates; our ability to effectively and efficiently integrate acquisitions into our business; higher than expected reserves and accruals particularly with respect to pension, taxes, insurance, and revenue; impact of changes in our residual value estimates and accounting policies, including our depreciation policy; unanticipated changes in fuel and alternative energy prices; unanticipated currency exchange rate fluctuations; fluctuations in inflation or interest rates; our ability to manage our cost structure; and the risks described in our filings with the Securities and Exchange Commission (SEC). The risks included here are not exhaustive. New risks emerge from time to time, and it is not possible for management to predict all such risk factors or to assess the impact of such risks on our business. Accordingly, we undertake no obligation to publicly update or revise any forward-looking statements, whether as a result of new information, future events, or otherwise. Note Regarding Non-GAAP Financial Measures: This presentation includes certain non-GAAP financial measures as defined under SEC rules, including: Comparable Earnings Measures, including comparable earnings from continuing operations; comparable earnings per share from continuing operations; and comparable earnings before income tax. Additionally, our adjusted ROE (ROE) measure is calculated based on adjusted earnings items. Operating Revenue Measures, including operating revenue, operating revenue growth and EBT as a percentage of operating revenue, in each case for Ryder and its business segments. Cash Flow Measures, including total cash generated and free cash flow. Refer to Appendix - Non-GAAP Financial Measures for reconciliations of the non-GAAP financial measures contained in this presentation to the most comparable GAAP measure. Additional information regarding non-GAAP financial measures as required by Regulation G and Item 10(e) of Regulation S-K can be found in our most recent Form 10-K, Form 10-Q, and Form 8-K filed with the SEC as of the date of this presentation, which are available at http://investors.ryder.com. All amounts subsequent to January 1, 2017, have been recast to reflect the impact of the lease accounting standard, ASU2016-02, Leases. Amounts throughout the presentation may not be additive due to rounding.

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Agenda 4 Welcome and Opening Remarks Calene Candela VP, Investor Relations Ryder Next Horizon: Transformation Unleashed Robert Sanchez Chairman & CEO Disrupting and Leading the Industry with Practical Innovation Karen Jones EVP, CMO, & Head of New Product Development Supply Chain Solutions: Perfecting Supply Chains with Vertical Expertise and Integrated Solutions Steve Sensing President, Supply Chain Solutions & Dedicated Transportation Solutions Q&A Session + Break Dedicated Transportation Solutions: Accelerating Scale and Density Steve Martin EVP, Dedicated Transportation Solutions Fleet Management Solutions: Enhancing Returns and the Customer Experience Tom Havens President, Fleet Management Solutions Clear Financial Strategy to Deliver Enhanced Returns John Diez EVP & CFO Ryder Next Horizon: Invest with Us Robert Sanchez Chairman & CEO Q&A Session Leadership Luncheon & Solutions Showcase 8:30 am 9:45 am 10:20 am 11:30 am 12:00 pm

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Ryder Next Horizon: Transformation Unleashed ROBERT SANCHEZ Chairman & Chief Executive Officer 5

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Video: Behind the Scenes in Daily Life 6

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Key Messages 7 Note: Includes Non-GAAP Financial Measures, such as ROE. Please see Appendix – Non-GAAP Financial Measures for the reconciliation to the GAAP Financial Measure. Industry leader driving outperformance through the cycle with complementary portfolio addressing customers' needs01 Achieved significant transformative milestones reflecting execution of balanced growth strategy 02 Next phase of strategy focused on accelerating profitable growth supported by operational excellence and customer-centric innovation 03 Transformed business model and strategic initiatives support increased long-term Adjusted ROE (ROE) target04

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Ryder 2023 Snapshot (NYSE: R) 21% 18% 15% 13% 10% 7% 5% 5% 6% Food & Beverage Retail & Consumer Goods Transportation & Logistics Automotive Industrial Housing Technology Business & Personal Services Other DIVERSIFIED CUSTOMER BASE1 8 1933 Founded $11.8B Total Revenue2 ~47,500 Employees3 ~41,000 Commercial Customers ~760 Maintenance Locations >100M sq. ft. Warehouse Space2 248,900 Vehicles Managed4 $10B Freight Under Management 1 As % of Operating Revenue (a non-GAAP financial measure) as of 12/31/2023. Please see Appendix – Non-GAAP Financial Measures for the reconciliation to the GAAP Financial Measure. 2 This amount results from continuing operations. 3 Full-time employees as of 12/31/2023. 4 2023 average vehicle count. Leading Provider of Outsourced Logistics and Transportation Solutions in North America

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Complementary Business Segments Provide Broad Range of Value-added Solutions 9 BUSINESS SEGMENT SYNERGIES & RELATED BENEFITS FMS Vehicle leasing and rental, maintenance, and support services DTS Drivers, routing, scheduling, and administration SCS Distribution / transportation management, dedicated transportation, brokerage, e-commerce, and last mile Equipment & Maintenance ~34K DTS / SCS vehicles are leased and maintained by FMS Asset Management Redeployed ~6,700 vehicles in 2023 Revenue Synergies ~50% of new sales in DTS are from FMS upsell opportunities DTS / SCS Shared Resources Technology • driver recruiting logistics engineering • brokerage FMS shop footprint Cost and operating efficiencies Manage rental utilization, cost, and operating efficiencies FMS upsell increases revenue 4-5x and margin 2-3x on same vehicle investment Scale and cost efficiencies

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Culture Grounded in Our Vision, Mission, and Values 10 Vision and Values Fundamental to Enabling Our Ability to Grow Profitably OUR VALUES Trustworthy Integrity anchors us in everything we do. We live by our word and actions. We work together to perform our best and hold ourselves accountable. Determined We use our expertise to ensure our customers achieve their goals every day. We develop optimal solutions for both conventional and complex problems. We are never satisfied with the status quo. Responsible Our priority on safety, sustainability, and charitable giving, makes the communities where we live and work thrive. VISION To perfect the supply chains that drive our economy MISSION To responsibly deliver innovative supply chain and transportation solutions that are reliable, safe, and efficient, enabling our customers to deliver on their promises

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS 11 In 2019, We Announced Our Balanced Growth Strategy

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Implemented and Executed Transformative Actions 12 Accelerated Growth in Higher-return SCS and DTS with Moderate Growth and Increased Returns in FMS  Lowered residual value estimates; reduced reliance on used vehicle proceeds to achieve returns and likelihood of losses on used vehicles sold  Exited sub-performing FMS UK business  Enhanced Asset Management Playbook resulted in higher returns vs. prior cycles  Strengthened SCS and DTS contracts to facilitate cost pass-throughs  Drove value-based pricing discipline across all segments  Achieved $100M+ in annual maintenance cost savings  Expanded retail used vehicle sales vs. wholesale  Enhanced rental truck-tractor mix  Maintained strong balance sheet  Completed strategic acquisitions (Midwest, Whiplash, Baton, Dotcom, IFS, and Cardinal)  Added and enhanced capabilities in SCS  Increased scale and density in DTS  Returned capital to shareholders De-risk and Optimize the Model Enhance Returns and Free Cash Flow Drive Long-term Profitable Growth

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS We Have Transformed 13 Note: Includes Non-GAAP Financial Measures, such as Comparable EPS and ROE. Please see Appendix – Non-GAAP Financial Measures for the reconciliation to the GAAP Financial Measure. Expected Post-transformation Trough Returns (2024F) to be Well Above Pre-transformation Peak Returns (2018) 2018: Pre-transformation Freight Cycle Peak 2024F: Ryder Today Expected Freight Cycle Trough CHANGE (∆) Revenue Mix $8.4B ~$13B +16 pts (SCS / DTS) Comparable EPS $5.95 $11.75 – $12.50 ~2X ROE 13% 15.5% – 16.5% +250 – 350 bps SCS 3-year Revenue CAGR 16% 20% +400 bps Operating Cash Flow $1.7B $2.4B +40% 56% 44% 40% 60% FMS SCS / DTS

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Structural Changes Have Significantly Improved Earnings 14 Well-Positioned for Structurally Higher Quality Earnings Note: Includes Non-GAAP Financial Measures, such as Comparable EPS. Please see Appendix – Non-GAAP Financial Measures for the reconciliation to the GAAP Financial Measure. 1 Represents high end of $11.75 - $12.50 comparable EPS forecast range 2018 Comparable EPS Prior Cycle Peak SCS / DTS Profitable Growth +$2.50 $5.95 FMS New maintenance initiative, lease pricing, growth KEY EARNINGS DRIVERS Shares / Other +$2.60 +$1.45 $12.501 2024F Comparable EPS Expected Cycle Trough

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Significant Growth Opportunities within Large Total Addressable Markets 15 1 Sources: Polk / IHS, Armstrong & Associates, Ryder estimates. Well-positioned for Continued Growth At or Above Market $256B ~18% Outsourced1 $29B ~4% Outsourced1 $20B ~25% Outsourced1 $1.4T Addressable Market1 Supply Chain Solutions $80B Addressable Market1 Fleet Management Solutions $660B Addressable Market1 Dedicated Transportation Solutions Non-outsourcedOutsourced

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Secular Trends Are Driving Demand for Outsourcing 16 Providing Solutions that Address Growing Challenges in Transportation and Logistics DYNAMIC SUPPLY CHAINS LABOR CONSTRAINTS INCREASING COSTS AND COMPLEXITY; GOVERNMENT INCENTIVES AND REGULATIONS DISRUPTIVE TECHNOLOGIES, OMNICHANNEL, AND ENERGY TRANSITION Focus on resilient and flexible supply chains Increased interest in nearshoring / onshoring Labor challenges pressure driver, technician, and warehouse worker shortages Higher vehicle maintenance and purchase costs Infrastructure investment incentives; changes to emissions standards and safety regulations Autonomous trucking, technology-enabled asset sharing and data analytics E-Commerce and final mile growth trends Low / zero emission powertrains, infrastructure support

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Strategy is Delivering Improved Returns and Capacity to Invest in Innovation and Growth 17 Next Phase of Balanced Growth Strategy Builds on Transformed Business Model Invest in Customer-centric Innovation Further Improve Full-cycle Returns and Generate Profitable Growth Create Compelling Value through Operational Excellence

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Create Compelling Value through Operational Excellence 18 Driving Next Level of Transformation with Our Focus on Continuous Improvement KEY STRATEGIC INITIATIVES Leverage multi-client networkSCS Continue to deploy Ryder Flex operating structure DTS FMS Continuous improvement process to drive maintenance and operations efficiencies • Well-positioned to benefit from long-term growth trends • Improve efficiencies while driving increased customer service levels • New $50M multi-year maintenance cost savings initiative

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS SELECT CUSTOMER-FACING TECHNOLOGIES Investing in Customer-centric Innovation to Lead the Industry 19 Technology-agnostic Approach to Disrupt and Innovate within Our Industry RYDERSHARE RYDERGYDE RYDERVIEW ACQUISITION SPOTLIGHT • First invested in Baton through RyderVentures in 2021; completed acquisition in August 2022 • Pioneering a suite of groundbreaking customer-facing technologies to revolutionize how customers interact with their transportation and supply chain networks • Creating a first-of-its-kind AI-powered digital platform and optimization engine • Real-time visibility of shipments and orders • Seamless integration for efficient tracking, reliable data, and exception management • Single unified platform to optimize on-time deliveries and minimize issues • Application that manages all aspects of a fleet anywhere, anytime, and on any device • Fleet management • Fueling solutions • Customer service • Leading last mile technology platform that provides complete control to ensure on-time delivery • 100% real-time visibility • Simplified scheduling • Routing and tracking • Advanced analytics • Leading e-commerce technology that simplifies fulfillment • Provides real-time data for • Orders • Inventory management • Order tracking • Returns management RYDERSHIP

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Further Improve Full-cycle Returns and Generate Profitable Growth 20 Building on a Strong Foundation to Accelerate Returns 1 Compared to FY18. KEY STRATEGIC INITIATIVES Expand share of wallet within vertical subsegmentsSCS Integrate Cardinal acquisition to realize synergies and benefit from top-grade talent DTS FMS Differentiate lease pricing with focus on higher return segments • Cross-sell co-packaging / co-manufacturing within CPG and expand to other verticals • $40M – $60M synergies expected in 2026 • Lease pricing full annual benefit of $125M1 expected to be realized in 2025

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Clear Path to Higher Returns 21 Increasing ROE Target Over the Cycle +300bps ROE ROE Prior Target Over the Cycle High Teens New Target Over the Cycle FMS New maintenance initiative, lease pricing, growth SCS / DTS e-Comm and RLM optimization, acquisition synergies, flex operating structure, growth Low Twenties +300 bps ROE Note: Includes Non-GAAP Financial Measures, such as ROE. Please see Appendix – Non-GAAP Financial Measures for the reconciliation to the GAAP Financial Measure.

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Transformed Business Model Poised to Deliver Higher Highs 22 Well-positioned to Exceed Prior Peak Record Earnings Note: Includes Non-GAAP Financial Measures, such as Comparable EPS. Please see Appendix – Non-GAAP Financial Measures for the reconciliation to the GAAP Financial Measure. 1 Represents high end of $11.75 - $12.50 comparable EPS forecast range 2024F Comparable EPS Expected Trough $16.37 Record 2022 results include outsized UVS gains and rental 2022 Comparable EPS Prior Peak Exceeding Prior Peak (2022: $16.37) Comparable EPS Next Peak Contractual growth Strategic initiatives Share repurchases UVS and rental CYCLE DOWNTURN UVS and rental Contractual growth Strategic initiatives CYCLE UPTURN $12.501

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Long-term Financial Model 23 Business Momentum Set to Deliver Higher Returns Over the Cycle Targets defined as: High Teens - 17% to 19%, Low Twenties - 20% to 22%, LDD - 10% to 12%, Low Teens - 13% to 14%. HSD: High-Single-Digit. MSD: Mid-Single-Digit. LDD: Low-Double-Digit. Note: Includes Non-GAAP Financial Measures, such as ROE, Operating Revenue, and EBT % of Operating Revenue. Please see Appendix – Non-GAAP Financial Measures for the reconciliation to the GAAP Financial Measure. ROE High Teens Low Twenties Operating Revenue Growth Total Ryder HSD HSD Fleet Management MSD MSD Supply Chain LDD LDD Dedicated HSD HSD EBT as % of Operating Revenue Fleet Management LDD Low Teens Supply Chain HSD HSD Dedicated HSD HSD Leverage (Debt-to-equity) 2.5x – 3.0x 2.5x – 3.0x PRIOR TARGETS NEW TARGETS

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Sustainability at Ryder 24 Sustainability Initiatives Reflect Our Commitment to Managing Operations Responsibly • Optimizing customer supply chains to reduce costs and environmental impacts • Achieved targets to reduce Scope 1 (10%), Scope 2 (30%), and Scope 3 (15%) emissions • 2023 CDP Climate Change Response received A scores in emissions reporting and reduction initiatives, which includes 3rd-party verification • U.S. EPA SmartWay "High Performer" truck carrier, top 2% for environmental performance Environmental • Lytx in-cab safety program resulted in ~60% reduction in collisions since 2019 • 65K voluntary submissions to our "GoodCatch" safety program, driving proactive employee identification and corrective action • U.S. DHS Safety Act, C-TPAT, and Fast Program certified, enhancing our ability to securely expediate goods across the U.S. border Safety, Security, and Preparedness • Maintain pay parity for employees of color and women at the professional and managerial levels, verified by an annual pay gap assessment • Our Future Leader Program advances frontline employee careers with a 28% promotion rate (2021-2023) • 8% of directly controllable procurement spend goes to minority, woman, and veteran-owned businesses Diverse Workforce and Supplier Network • Cybersecurity program is certified to ISO 27001 and evaluated annually by external experts • All employees (~50K) completed compliance and ethics trainings in 2023 • Our enterprise risk management program is periodically assessed by an independent 3rd-party and continuously improving Governance Note: See our Corporate Sustainability Report for more information at ryder.com/sustainability.

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Accountable and Engaged Board of Directors – Expertise and Experience Support our Long-term Vision Robert Sanchez Robert Eck Robert Hagemann Michael Hilton Tamara Lundgren Luis Nieto Chairman & CEO, Ryder Lead Independent Director, Ryder and Former Director & CEO, Anixter International Former SVP & CFO, Quest Diagnostics Former President & CEO, Nordson Corporation President & CEO, Radius Recycling Former President, Consumer Foods Group, ConAgra Foods, Inc. David Nord Abbie Smith E. Follin Smith Dmitri Stockton Charles Swoboda Former Chairman & CEO, Hubbell Incorporated Boris and Irene Stern Distinguished Service Professor of Accounting at University of Chicago Booth School of Business Former EVP, CFO & Chief Administrative Officer, Constellation Energy Group, Inc. Former SVP & Special Advisor to the Chairman, General Electric Company Former Chairman and CEO of CREE, Inc. (Wolfspeed, Inc.) 25 91% Independent Directors 54% Gender / Racial / Ethnic Diversity 91% 91% 91% 73% 64% 64% BOARD ATTRIBUTES SKILLS PROFILE Financial & Accounting Branding / Strategy Industry Experience C-suite Leadership Business Development & M&A Public Company Operations Strong Lead Independent Director

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Robert Sanchez Karen Jones Steve Sensing Steve Martin Tom Havens John Diez Chairman & CEO Joined: 1993 EVP, CMO 2013 President, SCS & DTS 1992 EVP, DTS 1988 President, FMS 1993 EVP, CFO 2002 Cycle-tested and Execution-focused Leadership Team 26 220+ Years Combined Industry Experience T O D A Y ’ S P R E S E N T E R S A D D I T I O N A L E X E C U T I V E L E A D E R S H I P Robert Fatovic Sanford J. Hodes Frank Lopez Rajeev Ravindran EVP, Chief Legal Officer and Corporate Secretary 1994 SVP, Chief Procurement and Corporate Development Officer 2002 EVP, Chief Human Resources Officer 2002 EVP, Chief Information Officer 2018 Most of Team Has Executed 20+ Years Together

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Disrupting and Leading the Industry with Practical Innovation Karen Jones EVP, CMO, & Head of New Product Development 27

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Investing in and developing emerging technologies that holistically address customer needs and lead the industry01 Customer-centric, technology-agnostic mindset enables the widest breadth of innovation02 Disciplined, strategic approach to innovation driving long-term value03 Key Messages 28

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS 29 Designed to Solicit Guidance and Ideation on New Products, Solutions, and Partnerships OBJECTIVES • Create a forum of thought leaders across industries to shape our future solution development • Preview and influence our strategic direction, initiatives, and technology roadmap • Provide collaborative insight to help improve our business in markets served CAB PROGRAM BACKGROUND • Launched in 2014 • 60+ Ryder customers • Fortune 500 and large private companies • VPs as well as supply chain and fleet executives • Industries represented: automotive, retail, healthcare, apparel, technology, CPG, and food & beverage SELECT CAB PARTICIPANTS TECHNOLOGY SPOTLIGHT RyderShare developed and launched through CAB program Customer-centric Innovation Ryder Customer Advisory Board (CAB) Programs

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS BUILD: Strategic Investments Built on Customer-driven Need for Innovative Solutions 30 BENEFITS • Creating customer stickiness and driving incremental value to win new business (e.g., RyderShareTM helps drive ~35% of new business revenue in SCS / DTS) • Improving customer experience and driving operational efficiencies • Expanding wallet share with new and existing customers through differentiated portfolio of solutions • Leveraging deep partnerships to innovate and lead the transportation logistics industry DIGITAL TECHNOLOGIES E-COMMERCE ASSET SHARING EV / AV RYDEROPSBOXTM RYDERELECTRIC+TM

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Video: Ryder-built Technology 31

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS PARTNER: Strategic Investments Built on Customer-driven Need for Innovative Solutions 32 BENEFITS • Creating customer stickiness and driving incremental value to win new business (e.g., RyderShareTM helps drive ~35% of new business revenue in SCS / DTS) • Improving customer experience and driving operational efficiencies • Expanding wallet share with new and existing customers through differentiated portfolio of solutions • Leveraging deep partnerships to innovate and lead the transportation logistics industry RYDEROPSBOXTM DIGITAL TECHNOLOGIES E-COMMERCE ASSET SHARING EV / AV RYDERELECTRIC+TM

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Chargers & EVCI Complete EVCI solution: design | install | lease maintain | operate Electrification Advisors Develop plan for EV with advisors and compliance specialists throughout your Ryder lease Lease or Finance Vehicle Access supply and financing for EVs Well-positioned to Assist Customers When Ready to Transition to EVs 33 Enabling the Electrification of Fleets as Technology Evolves RYDER ELECTRIC + | RYDER’S TURNKEY ELECTRIC VEHICLE SOLUTION Leading the industry in transportation and digital applications Telematics & On-road Technology Ensure smooth ops, actionable data; digital technology and roadside assistance Maintenance Timely preventive and unscheduled maintenance Total Cost of Transport: while light duty is relatively on par with ICE counterparts, heavy duty costs ~>2x that of ICE counterparts Infrastructure: charging installation timelines up to 2 years, and public charging and on-site power availability remains limited Regulation remains volatile with evolving enforcement timelines and requirements FACTORS AFFECTING ADOPTION Launched: May 2023 Mobile maintenance offering via Torque positions us for evolving heavy-duty maintenance requirements Opportunity to enter light-duty space

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS RYDEROPSBOXTM BUY: Strategic Investments Built on Customer-driven Need for Innovative Solutions 34 BENEFITS • Creating customer stickiness and driving incremental value to win new business (e.g., RyderShareTM helps drive ~35% of new business revenue in SCS / DTS) • Improving customer experience and driving operational efficiencies • Expanding wallet share with new and existing customers through differentiated portfolio of solutions • Leveraging deep partnerships to innovate and lead the transportation logistics industry DIGITAL TECHNOLOGIES E-COMMERCE ASSET SHARING EV / AV RYDERELECTRIC+TM

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS BENEFITS Ryder Freight Ecosystem: Built through Baton (2024 – 2027 Timeline) 35 Delivering on Perfecting Supply Chains Increasing visibility and cross-sell opportunities across all segments Capturing freight moves across all of Ryder Providing comprehensive view of entire business portfolio to create and extract maximum value Customer Facing Technology RyderShareTM RyderGydeTM AI Optimization Truck GPS Data Driver Data Customer Data Load Data Standardized Data Platform Internal Facing Technology Operator Execution Platform Ryder TMS Trucks Drivers Loads Inventory Enabling Ryder Flex operating structure

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Neuraflash Case summary and routing to Ryder Customer Response Center Baton Products Revolutionary TMS and visibility tools Opportunity: Prudent, Strategic Approach to AI 36 Large Potential for AI Applications in the Early Stages of Development CUSTOMER FACING PRODUCT DEVELOPMENT BUSINESS PROCESS IMPROVEMENT APPS Incorporation of AI into our technology products to provide unparalleled value to our customers by using our own deep data knowledge IT and Operations evaluating use cases and off-the- shelf applications as well as in-house development to improve customer service and drive operational efficiencies TIMEFRAME FUTURENOW

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS RyderVentures: Our Goal is to Invest $50M Over 5 Years… 37 …in Disruptive Technologies that Support Our Customer-centric, Strategic Approach to Innovation SELECT INVESTMENT SPOTLIGHT RYDERVENTURES APPROACH Invested in 15 companies to date Strategic-focused investor vs. financial-only investor ‘Seed’ through ‘C’ round investments Early test bed to pilot technology and prove business models – early design partner Take key learnings to influence strategic roadmap and new product development Fits into our build, partner, buy strategy

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS 38 Key Takeaways Investing in and developing emerging technologies that holistically address customer needs and lead the industry 01 Customer-centric, technology-agnostic mindset enables the widest breadth of innovation 02 Disciplined, strategic approach to innovation driving long-term value 03 RYDEROPSBOXTM RYDERELECTRIC+TM

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Supply Chain Solutions Perfecting Supply Chains with Vertical Expertise and Integrated Solutions STEVE SENSING President, Supply Chain Solutions & Dedicated Transportation Solutions 39

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Supply Chain Solutions Key Messages 40 Strengthening capabilities in growing verticals through investments in customer-facing technology and strategic acquisitions 04 Strengthening market leadership as provider of integrated logistics solutions from port-to-door across North America01 Capturing large and growing market opportunity through deep industry expertise supported by data-driven insights02 Operational excellence leverages data analytics, value- based automation and LEAN principles to create value03

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Supply Chain Solutions Snapshot 41 Note: Includes Non-GAAP Financial Measures, such as Operating Revenue, EBT % of Operating Revenue, and Comparable EBITDA. Please see Appendix – Non-GAAP Financial Measures for the reconciliation to the GAAP Financial Measure. 1 Represents total for all Ryder System, Inc. PORT-TO-DOOR INTEGRATED SUPPLY CHAIN SOLUTIONS (% of 2023 SCS Revenue) 2023 PERFORMANCE $4.9B Total Revenue $3.6B Operating Revenue 6.4% EBT as % of Operating Revenue $375M Comparable EBITDA 2023 OPERATING STATISTICS >100M+ sq. ft. Warehouse Footprint $10B Freight Under Management1 ~13,800 Total Vehicles +900 Customer Accounts 32% Dedicated Transportation 10% Transportation Management and Brokerage 35% Distribution Management 4% Value-added Services 19% e-Commerce Fulfillment and Last Mile Delivery

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Supply Chain Solutions Transformation Unleashed 42 Significant Achievements with Long Runway Ahead for Profitable Growth 1 % of 2023 SCS Operating Revenue (a non-GAAP financial measure). Please see Appendix – Non-GAAP Financial Measures for the reconciliation to the GAAP Financial Measure. Balanced and diversified revenue mix 33% 26% 29% 12% Omnichannel Retail CPG Automotive Industrial & Other KEY MILESTONES SINCE 2019 1 2023 Vertical Mix1  Adjusted contract terms to facilitate quicker and more efficient cost recovery 2 Focused on disciplined value-based pricing and enhanced contracts 3 Increased customer value through data- driven insights and technology 4 Completed integration of acquisitions  Continuous improvement  Ryder OpsBoxTM labor mgmt. tool  Data analytics  Automation   

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Significant Market Opportunity Enabling Robust Growth 43 1 Sources: Polk / IHS, Armstrong & Associates, Ryder estimates. Large Market with Secular Trends Favoring Outsourcing CAPTURING OPPORTUNITY FROM SECULAR TRENDS FAVORING OUTSOURCING STRENGTHENING CAPABILITIES WITHIN HIGH PERFORMING VERTICALS THROUGH TARGETED ACQUISITIONS DEMAND FOR SUPPLY CHAIN RESILIENCE LABOR SHORTAGE E-COMMERCE NEARSHORING / ONSHORING $256B ~18% Outsourced1 $1.4T Addressable Market1 Supply Chain Solutions CONTINUED INVESTMENT IN CUSTOMER-FACING TECHNOLOGY Non-OutsourcedOutsourced

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Supply Chain Solutions Sustainable Competitive Advantages 44 Market Leader Providing Value-added Integrated Solutions across Key Verticals NORTH AMERICA FOCUSED INTEGRATED SUPPLY CHAIN SOLUTIONS • Seamless customer service across N.A. • Streamlined cross-border capabilities • Expertise in managing complex supply chains • Design and operate an integrated suite of supply chain solutions ENABLING TECHNOLOGIES AND CONTINUOUS IMPROVEMENT • Visibility and IT capabilities • LEAN expertise • Engineering and automation excellence • Digitization of warehouse workflow DEEP VERTICAL EXPERTISE • Differentiated knowledge and expertise across key verticals – Automotive – Consumer packaged goods – Industrial and other – Omnichannel retail

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS ~70% of SCS Revenue from Customers Leveraging Multiple Port-to-Door Solutions1 Integrated Port-to-Door Solutions across Key Verticals 45 1 Based on 2023 SCS revenue. Transportation Management • Drayage transportation • Design and manage networks of for-hire carriers • Freight Brokerage • Cross-border Transportation Dedicated Transportation • Design, manage, and operate networks of vehicles and drivers primarily for automotive, industrial, and retail customers Distribution Management • Design, manage, and operate networks of warehouses and cross-docks • Perform value- added services (i.e., packaging) e-Commerce Fulfillment • Expanded with Whiplash (2022) • Pick, pack, and ship retail and online orders • Facilitate small parcel delivery to home Last Mile Delivery • Expanded with MXD (2018) • Assemble big and bulky items • Deliver to room of choice Value-added Services • Added co-mfg. and co-packaging with IFS (2023) • Assembly of products CAPABILITIES ENHANCED THROUGH STRATEGIC ACQUISITIONSCORE SUPPLY CHAIN SOLUTIONS

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS BACKGROUND Expanding CPG Vertical Wallet Share through Recent IFS Acquisition 46 CA UT TX GA FL NC PAOH IL IFS OFFERINGSBACKGROUND • Identified need of top customers for co-packaging and co- manufacturing services • Acquired IFS in November 2023 to address industry need • Proven model in food and non-food products • 15 multi-client and dedicated operations • 180+ customers in CPG, retail, and healthcare DELIVERING VALUE Customer Value • Ryder is now a one-stop-shop for customers with added co-packing and co-manufacturing capabilities Ryder Value • Highly complementary additional capabilities that will round out our comprehensive suite of services • Co-packing / manufacturing high growth and high margin profile will be accretive on a pro-forma basis • Up / cross-sell opportunities applicable to other verticals IFS Providing Synergies for Ryder and Our Customers

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Case Study: Lead Logistics Provider for General Motors 47 Leading Automotive OEM Leveraging Multiple SCS Solutions across a Complex North American Supply Chain UNIQUE OFFERINGBACKGROUND RYDER VALUE • Proprietary technology provides best- in-class visibility to enable a plan for every part • Ability to adapt solutions for emerging EV supply chains • Strong focus on continuous improvement, root cause corrective action plans, and process automation efforts across North America • Recognized with prestigious “Supplier of the Year” award 11 times and honored with Safety Award in 2022 • Need for a leading logistics provider with supply chain and manufacturing services to support US and Canadian operations – 40+ manufacturing sites – 3,000+ employees • Chose Ryder to optimize and manage inbound supply chain across U.S., Mexico, and Canada, including $1B+ in freight under management Full suite of value-add supply chain and manufacturing support services Route design Transportation management Dedicated transportation Inbound to mfg. and value-added services Multi-channel crossdocking Finished vehicle support and outbound logistics Cross-border services Returnable container management

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS UNIQUE OFFERINGBACKGROUND RYDER VALUE • Seamless start-up and operational performance built trust with customer’s leadership • 100% real-time visibility of shipments across Pabst’s transportation network • Saved $442K in procurement in year one Case Study: Quenching a Thirst for Supply Chain Visibility and Optimization 48 Innovation and Operational Excellence Leading to Deep Partnership with a 175-year Old Company We chose Ryder because they were in-tune with our business. Ryder understood what we wanted, jumped in, and brought more than just a single solution. Having that is huge. Ryder is always looking ahead at how we can get better than we are today.” Seamlessly implemented RyderShareTM real- time visibility tool during peak season Transformative digitization of Pabst’s transportation network to bring stability, scalability, and visibility to growing network Increased dock visibility and planning through Ryder’s proprietary dock scheduler Deployed business intelligence and reporting on day 1, enabling network controls and continuous improvement • Faced with challenges of an evolving beverage landscape, Pabst Brewing recognized need to optimize its transportation network and enhance visibility across its supply chain • In 2022, Pabst outsourced their domestic transportation management operations to Ryder SVP of Supply Chain, Pabst Blue Ribbon

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Case Study: Omnichannel End-to-End Fulfillment at Stance Socks 49 One-stop Port-to-Door Solutions for Omnichannel Retailers RYDER VALUE • Ability to offer port-to-door solutions • Leading-edge automation, engineering, and technology capabilities • Well-positioned to scale up or down with customers volume as needed • With established service level agreements, SOPs, and continuous improvement initiatives, Ryder has helped Stance achieve key results: 1 On-time product delivery 2 Delivering revenue 3 Doing both of these, profitably We’re seeing a commitment to excellence within our new structure at Ryder, and our main goal is to continue to evolve this relationship. From exploring seamless returns to establishing new fulfillment goals, Ryder will be a key partner in helping us continue to improve our customer experience.” Vice President of Operations, Stance Socks UNIQUE OFFERINGBACKGROUND • Growing apparel brand needed assistance with demand planning • Desired an omnichannel logistics partner with capabilities to scale end-to-end fulfillment • Chose Ryder as a partner that could manage surge in orders when needed

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Supply Chain Solutions Strategic Initiatives 50 Continued Focus on Profitable Growth Further Improve Full-cycle Returns and Generate Profitable Growth Invest in Customer-centric Innovation Create Compelling Value through Operational Excellence • Leverage multi-client network • Continuous improvement mindset leverages value-based automation, robotics, and AI to improve efficiencies • Continue to invest in customer-facing technology (i.e., RyderShareTM, RyderShipTM, Ryder OpsBoxTM, and RyderViewTM) to drive efficiencies and enhance customer experience • Expand share of wallet within vertical subsegments • EverBetterTM logistics marketing campaign • Promote nearshoring capabilities

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS OUR CULTURE OF CONTINOUS IMPROVEMENT WITHIN SUPPLY CHAIN SOLUTIONS… • Encourage employee suggestions through “thousands of little ideas” • Challenge every aspect of process to get better • Standardized LEAN Warehouse Template • Ryder OpsBoxTM labor management tool with proprietary visual management technology • Ryder rewards program • Application and sharing of best practices across industry verticals through centralized department of supply chain excellence Structured Continuous Improvement and Customer Engagement Model 51 Continuous Improvement Philosophy to Accelerate Operational Excellence Driving Customer Success through Data Analytics, Automation, and Continuous Improvement Rollout / Realize Benefits START Recognize Opportunity Collaborative Customer Design Solution Implement Process and Value-based Automation Leverage Data Analytics Implement Solution with Startup Effectiveness Team

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Video: BJC Supply Chain Transformation 52

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Supply Chain Solutions: Key Takeaways 53 Strengthening market leadership as provider of integrated logistics solutions from port-to- door across North America Capturing large and growing market opportunity through deep industry expertise supported by data- driven insights Operational excellence leverages data analytics, value-based automation and LEAN principles to create value 01 02 03 Strengthening capabilities in growing verticals through investments in customer-facing technology and strategic acquisitions 04 LDD Operating Revenue Growth HSD EBT as % of Operating Revenue LONG-TERM TARGETS Note: Includes Non-GAAP Financial Measures, such as Operating Revenue and EBT % of Operating Revenue . Please see Appendix – Non-GAAP Financial Measures for the reconciliation to the GAAP Financial Measure.

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Q&A 54

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS BREAK 55

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Dedicated Transportation Solutions Accelerating Scale and Density STEVE MARTIN EVP, Dedicated Transportation Solutions 56

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Dedicated Transportation Solutions Key Messages 57 Acquisition integration is on track with meaningful synergies expected02 Drive operational efficiencies by leveraging increased scale and density of combined businesses and digitization03 Well-positioned to continue to drive profitable growth and benefit from cycle upturn04 Strengthened position as a leading provider of dedicated transportation solutions through Cardinal acquisition 01

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS 2023 PERFORMANCE $1.8B Total Revenue $1.3B Operating Revenue 9.3% EBT as % of Operating Revenue $121M Comparable EBITDA Dedicated Transportation Solutions Snapshot 58 Note: Includes Non-GAAP Financial Measures, such as Operating Revenue, EBT % of Operating Revenue, and Comparable EBITDA. Please see Appendix – Non-GAAP Financial Measures for the reconciliation to the GAAP Financial Measure. ChoiceLease Vehicles and Maintenance Dedicated Transportation Solutions Technology, Visibility, and Optimization Professional Drivers and Management + + = DEDICATED TRANSPORTATION SOLUTIONS

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Dedicated Transportation Solutions Transformation Unleashed 59 On a Continuous Improvement Journey with Long Runway Ahead for Profitable Growth KEY MILESTONES SINCE 2019 1 Added scale and density to accelerate profitable growth  Completed Cardinal acquisition in Feb 2024 2 Improved quality of portfolio through enhanced contracts  ~95% of contracts have been restructured to facilitate quicker and more efficient cost recovery  Implementation of value- based pricing enabled DTS to reach EBT % target 3 Captured significant upselling opportunities and maintenance synergies through collaboration with FMS  ~50% new DTS sales from FMS collaboration  Maintenance benefits expected to be meaningful components of Cardinal synergies 4 Invested in industry-leading technologies and capabilities  RyderDriveTM: scalable, digitized trip management  RyderShareTM: end-to-end visibility and collaboration platform  Business intelligence: leveraging data analytics  In-cab safety programs: ~60% reduction in collisions Note: Includes Non-GAAP Financial Measures, such as Operating Revenue. Please see Appendix – Non-GAAP Financial Measures for the reconciliation to the GAAP Financial Measure.

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Significant Growth Opportunity from Large, Non-outsourced Private Fleet Market 60 Large Market with Secular Trends Favoring Outsourcing 1 Sources: Armstrong & Associates and internal Ryder estimates CAPTURING OPPORTUNITY FROM SECULAR TRENDS FAVORING OUTSOURCING RISING EQUIPMENT COSTS STRICTER SAFETY REGULATIONS BUILDING FOUNDATION TO ACCELERATE PROFITABLE GROWTH • Maintained pricing discipline and optimized contracts through customer portfolio management • Focused approach to building scale / density; well-positioned to grow profitably • Bringing unique business insights and visibility through differentiated solutions • Providing value-added services through specialized equipment, handling, and additional process activity at the delivery $29B ~4% Outsourced1 DRIVER SHORTAGE $660B Addressable Market1 Dedicated Transportation Solutions Non-OutsourcedOutsourced

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS FMS SYNERGY • Sales, purchasing power, and asset management • Leveraging FMS scale and access to vehicles • Vehicle uptime through preventative maintenance Dedicated Transportation Solutions Sustainable Competitive Advantages 61 Unique Capabilities Provide Value and Elevated Business Insights to Private Fleets DRIVER RETENTION • 100% company drivers, robust training program • Favorable work / life balance: ~85% of drivers home daily • Strong referral and recruiting programs • Flexible driver pools to support area surges OPERATIONAL EXCELLENCE • Recognized safety programs • Exceptional on-time delivery performance • Deep industry knowledge • Customized dedicated vs. commoditized LEADING-EDGE CUSTOMER TECHNOLOGIES • 100+ logistics engineers; optimizing routing and scheduling • RyderShareTM: visibility and collaboration platform • RyderDriveTM: digitized workstream and business intelligence platform • Proprietary Ryder TMS built by Baton

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Expected Results Cardinal Acquisition Completed in February 2024 62 Focused on Realizing Synergies and Returning to HSD EBT as a % of Operating Revenue Note: Includes Non-GAAP Financial Measures, such as Operating Revenue and EBT % of Operating Revenue. Please see Appendix – Non-GAAP Financial Measures for the reconciliation to the GAAP Financial Measure. 1 Includes DTS, Cardinal Logistics and SCS dedicated business (primarily SCS-Automotive). Ryder + Cardinal’s National Footprint $40M – $60M Expected annual savings in 2026 Synergies expected to return FY25 EBT% back to HSD target HSD EBT% 11,900 Combined Power Vehicles1 700+ Combined Operating Locations 14,000 Combined Professional Drivers1 +$1B Expected to add ~$1B in annualized total revenue and ~$800M in annualized operating revenue (85% in DTS, 15% in SCS)

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS 63 Cardinal Acquisition Integration Integration Activities Largely Expected to be Completed in 2025 with Full Benefits Realized in 2026 STRATEGIC BENEFITS • Adds scale and density in our existing dedicated business driving operating efficiencies and delivering better value • Highly diversified portfolio serving long-tenured, blue-chip customers • Solidifies Ryder as a leading provider in the attractive customized solution segment of Dedicated • Strong people and similar customer-centric cultures • Deep sales experience and relationships EXPECTED SYNERGIES MAINTENANCE Transition all vehicles to FMS platform – complete 1H24 LEASES Replace 3rd-party financing with Ryder ownership as leases mature EFFICIENCY Drive operating leverage beginning 2H24 and accelerating in 2025

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Dedicated Transportation Solutions Large, Diversified Customer Base 64 Delivering Differentiated Experience across Portfolio of ~300 Customers 1 Based on 2023 DTS Revenue. 2 As of 2/1/2024 – includes Cardinal. CUSTOMER COUNT BY INDUSTRY2 • Remain diversified within retail and CPG • Minimal customer overlap with Cardinal • Additional cross-sell opportunities with FMS / SCS 90% Customer Retention Rate1 >50% Sales Captured through FMS Upselling ~50% of New Accounts Were Private Fleet Conversions SELECT CUSTOMERS 2% 3% 9% 12% 13% 13% 23% 25% Other Energy Hi-tech/Healthcare Metals Construction CPG Retail Industrial

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Video: Compelling Value from Outsourcing Private Fleets 65

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS 66 Accelerate Growth and Expand Margins Dedicated Transportation Solutions Strategic Initiatives Further Improve Full-cycle Returns and Generate Profitable Growth Invest in Customer-centric Innovation Create Compelling Value through Operational Excellence • Deploy Flex operating structure • Leverage Brokerage to enhance Dedicated customer freight solutions • Leverage insights from RyderShareTM and data analytics to drive continuous improvement and enhance customer experience • Leverage Baton’s proprietary, early-stage freight optimization platform to further enhance benefits of Flex operating structure • Integrate Cardinal to realize synergies and benefit from top-grade talent • Continue to cross-sell with FMS / SCS and market to DIY private fleets

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Ryder Flex Transforms DTS Operating Structure 67 Improving Efficiencies While Driving Increased Service Levels to Our Customers Moving from a One-to-one Structure to a Shared Regional Operation While Retaining Dedicated Service and Support Commitments to Each Customer START Recognize Opportunity Evaluate and Define Problem Research and Gauge Benefit Ideate Solutions Implement New Process Prove and Refine Concept Test Controlled Environment Rollout / Realize Benefits FEATURES • New Baton proprietary technology for customer and regional optimization • Establish optimal mix of centralized and on-site operations • Enhanced standard operating procedures supported by LEAN principles and data science CUSTOMER BENEFITS • Enhanced resource flexibility and fewer empty miles • Increased driver retention • Leverages density within a region to work more efficiently

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Dedicated Transportation Solutions: Key Takeaways 68 Strengthened position as a leading provider of dedicated transportation solutions through Cardinal acquisition Acquisition integration is on track with meaningful synergies expected Drive operational efficiencies by leveraging increased scale and density of combined businesses and digitization 01 02 03 Well-positioned to continue to drive profitable growth and benefit from cycle upturn 04 HSD Operating Revenue Growth HSD EBT as % of Operating Revenue LONG-TERM TARGETS Note: Includes Non-GAAP Financial Measures, such as Operating Revenue and EBT % of Operating Revenue. Please see Appendix – Non-GAAP Financial Measures for the reconciliation to the GAAP Financial Measure.

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Fleet Management Solutions Enhancing Returns and the Customer Experience TOM HAVENS President, Fleet Management Solutions 69

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Fleet Management Solutions Key Messages 70 Strong execution through the cycle, well-positioned for profitable growth, and to benefit from cycle upturn01 Enhancing returns through maintenance initiatives and pricing discipline02 Improve customer experience through operational excellence and technology to enhance our competitive advantage 03

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS 2023 PERFORMANCE $5.9B Total Revenue $5.1B Operating Revenue $665M EBT Fleet Management Solutions Snapshot 71 2023 OPERATING STATISTICS ~250K Total Vehicles ~13K Contractual Customers ~4,800 Technicians ~760 Maintenance Shops 63% 23% 14% PRODUCT PORTFOLIO Providing Outsourced Transportation Services and Operational Excellence across North America Used Vehicle Sales1 ChoiceLease Contractual Full-Service Lease Commercial Rental SelectCare Contractual Maintenance OPERATING REVENUE MIX ChoiceLease Rental SelectCare Note: Includes Non-GAAP Financial Measures, such as Operating Revenue. Please see Appendix – Non-GAAP Financial Measures for the reconciliation to the GAAP Financial Measure. 1 Not included in Operating Revenue. Contractual

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS KEY MILESTONES SINCE 2019 1 Transformed maintenance operating model and implemented a structured continuous improvement process  Achieved initial $100M+ of annual savings through maintenance operating model transformation  Improved customer experience 2 Executed price segmentation initiatives to deliver higher returns  80% of power portfolio renewed with new pricing model  On track to achieve full $125M annual lease pricing benefit in 2025 3 Expanded Used Vehicle Sales retail capacity to deliver higher volume and improved proceeds  Sold ~30% more units in 2023  Achieved ~5% incremental proceeds per unit from higher retail mix  Proceeds above residual value estimates 4 Implemented our enhanced asset management playbook driving higher earnings across all phases of the freight cycle  Reduced lease fleet idle assets by ~2,500 units vs. 2018 pre-transformation  Improved EBT performance: 13% 2023 vs. 8% 2018 pre-transformation Fleet Management Solutions Transformation Unleashed 72 On a Continuous Improvement Journey with Long Runway for Profitable Growth

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS 57% 24% 19% 2023 Revenue 51+11-501-10 Customers by Fleet Count: CONTRACTUAL REVENUE BASE CONTRACTUAL FLEET MIX1 38% 33% 21% 8% SELECT CUSTOMERS~13K Contractual Customers ~90% Customer Retention Rate <2% Largest Customer Share of Revenue TrailersTractors Light-duty Trucks Medium-duty Trucks Fleet Management Solutions Large, Diversified Customer Base and Fleet Mix 73 Providing Value-added Services for Large, Diversified Customer Base 1 2023 FMS vehicle count.

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Large Addressable FMS Market to Achieve Growth Targets 74 Overall Market Opportunity Supports FMS Long-term Target of MSD Operating Revenue Growth Note: Includes Non-GAAP Financial Measures, such as Operating Revenue. Please see Appendix – Non-GAAP Financial Measures for the reconciliation to the GAAP Financial Measure. 1 Sources: Polk / IHS, Armstrong & Associates, Ryder estimates. WELL-POSITIONED TO CAPTURE GROWTH FROM SECULAR OUTSOURCING TRENDS INCREASED VEHICLE COST AND MAINTENANCE COMPLEXITY TECHNICIAN / LABOR SHORTAGES DEMAND FOR DIGITIZATION GOVERNMENT / SAFETY REGULATIONS ACCESS TO AND COST OF CAPITAL VEHICLES AND PARTS – SUPPLY CHAIN CHALLENGES $20B ~25% Outsourced1 $80B Addressable Market1 Fleet Management Solutions Non-OutsourcedOutsourced

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Fleet Management Solutions Sustainable Competitive Advantages 75 Outsourcing to Ryder Delivers Compelling Value and 10% – 20% Cost Savings vs. Ownership NETWORK SCALE – HIGH ENTRY BARRIER • ~760 maintenance shops established over 90-year history • Buying power with major OEMs and partners • ~65 used vehicle retail centers and digital sales capabilities DEEP MAINTENANCE EXPERTISE • Best-in-class maintenance processes with ~4,800 highly skilled technicians • Training programs using cutting-edge technologies • Industry-leading uptime • Warranty services for majority of OEMs CUSTOMER RISK MITIGATION • No residual value risk • Guaranteed maintenance costs • Fixed payment schedules DIGITAL PRODUCTS AND FLEXIBLE SERVICES • Industry-leading digital technology with RyderGydeTM • Custom service levels for ChoiceLease and SelectCare • Variable financing solutions Comprehensive Capabilities Span Full Spectrum of Fleet Transportation Needs

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS 76 Fleet Management Solutions Strategic Initiatives Enhancing Returns and the Customer Experience Further Improve Full-cycle Returns and Generate Profitable Growth Invest in Customer-centric Innovation Create Compelling Value through Operational Excellence • Maintenance continuous improvement – targeting incremental $50M savings • Proactive asset management – preparing for cycle upturn and emissions pre-buy • Invest in technology (e.g., RyderGydeTM) to enhance customer experience • Differentiate lease pricing with focus on higher return segments; achieve $125M annual benefit in 2025

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Leveraging Continuous Improvement to Enhance Returns 77 Delivered Initial $100M+ Savings; New Multi-year Initiatives Targeting Incremental $50M APPLYING CONTINOUS IMPROVEMENT WITHIN FLEET MANAGEMENT SOLUTIONS… • Clear toll-gate approach structured to mitigate risk and assure business value • Practical opportunities are evaluated, tested, and implemented …TO ENHANCE RETURNS • Captured initial $100M+ of annual maintenance savings • Introducing new multi-year maintenance initiatives targeting incremental $50M Structured Continuous Improvement Process to Evaluate, Test, and Implement Value Creating Ideas START Recognize Opportunity Evaluate and Define Problem Research and Gauge Benefit Ideate Solutions Implement New Process Prove and Refine Concept Test Controlled Environment Rollout / Realize Benefits

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Video: Driving Operational Excellence in Maintenance 78

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS STRENGTHENING DEMAND PLAYBOOK • Drive profitable lease sales • Invest rental growth capital in truck classes • Incorporate cyclical forecast into residual value estimates • Manage contract expirations to limit exposure in downturn • Target early replacement opportunities • Strategic pre-buy orders in advance of 2027 engine technology changes WEAKENING DEMAND PLAYBOOK • Extend lease contracts • Redeploy rental vehicles to lease, dedicated, and supply chain • Leverage expanded used vehicle retail sales network • Reduce used truck inventory as market starts to weaken • Reduce discretionary spend • Invest in rental early in the upturn In 2022, We Unveiled an Enhanced Asset Management Playbook… 79 Demand > Supply Supply > Demand Strengthening Demand Weakening Demand Current FREIGHT CYCLE …and its Successful Implementation Led to Higher Earnings in the Current Down Cycle, and Well Positions FMS for the Upturn

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS PRE-BUY CREATES OPPORTUNITIES • Lease: Securing new OEM production provides opportunities for replacement with existing customers and new growth from market demand • Rental: Higher upfront cost for new vehicles makes Rental more attractive • UVS: Older technology vehicles are expected to be worth more post technology change • Procurement: Avoid forthcoming cost increases Upcoming Pre-buy Cycle Expected to Provide Strategic Growth Opportunities 80 Pre-buy Expected to Create Opportunities for FMS to Capture Benefits by 2026 BACKGROUND • New EPA Emission standards for heavy duty vehicles set to take effect in 2027 • New compliant vehicles are expected to have a significantly higher purchase price • During past pre-buy cycles, demand for older technology vehicles, both new and used, have increased • In past pre-buy periods, maintenance complexity, including training and new tooling, pushed owners to outsourcing • OEMs expected to ramp to peak production capacity ahead of pre-buy – ACT expects 20% of production in 2026 will be pre-buy related

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS INTERNAL EFFICIENCIES Improved Uptime Proactive Alerts Streamlined Operations Benchmarks + Insights CUSTOMER VALUE ~9,000 Current Customers, ~65,000 Users Create Overhead Leverage Prevent Breakdowns Reduce Maintenance Costs RYDERGYDE Connecting Customers with Ryder Fleet Manager Vehicle Driver Shop Self-service Capabilities Real Time Status Updates Industry-leading fleet app that allows customers to manage all aspects of a fleet with seamless interaction Technology Spotlight: RYDERGYDE 81 70% of FMS Contractual Customers Utilizing Platform

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS SEGMENTED PRICING IS IMPROVING RETURNS AND SHIFTING FLEET MIX TO HIGHER RETURN VEHICLES • Rolled out new lease pricing segmentation in 2018; 80% of power portfolio completed as of year end 2023 • Additional ~10% of power fleet already contracted at new pricing model to be in-serviced over the next ~12 months • Segmenting by application, risk profile, asset type, etc. • Shifted lease fleet mix – ~4K sleeper tractors to trucks Segmented Lease Pricing and Focus on Higher Return Vehicles 82 Delivering Higher Overall Returns with Lower Risk % OF POWER PORTFOLIO RENEWED UNDER NEW PRICING MODEL 40% 80% 100% 2021 2023 2025 Target Annual Benefit Realized $90M $125M$45M

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Fleet Management Solutions Key Takeaways MSD Operating Revenue Growth Low Teens EBT as % of Operating Revenue LONG-TERM TARGETS Strong execution through the cycle, well- positioned for profitable growth, and to benefit from cycle upturn 01 Enhancing returns through maintenance initiatives and pricing discipline 02 Improve customer experience through operational excellence and technology to enhance our competitive advantage 03 83 Raising from LDD Note: Includes Non-GAAP Financial Measures, such as Operating Revenue and EBT % of Operating Revenue. Please see Appendix – Non-GAAP Financial Measures for the reconciliation to the GAAP Financial Measure.

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS 84 Clear Financial Strategy to Deliver Enhanced Returns John Diez EVP & Chief Financial Officer

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Above-market returns delivered to shareholders reflecting strategy execution01 Outperformance expected to accelerate based on enhanced quality of contractual portfolio and benefits from cycle upturn02 Increasing long-term ROE target03 Robust balance sheet capacity to invest in growth and return capital to shareholders04 Financial Key Messages 85 Note: Includes Non-GAAP Financial Measures, such as ROE. Please see Appendix – Non-GAAP Financial Measures for the reconciliation to the GAAP Financial Measure.

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Demonstrated Execution Resulted in Transformed Business Model 86 Improved and De-risked Model FMS EBT % Growing SCS and DTS Contribution REVENUE MIX SHIFT 2018 2023 SCS / DTSFMS 56% 44% 44% 56% Record Returns ROE 13% 0% -1% 21% 29% 19% 2018 2019 2020 2021 2022 2023 SCS / DTS Growth Bolstering Contractual Earnings SCS / DTS Earnings ($M) SCS / DTS EARNINGS Strategy Delivered Revenue and Earnings Growth and Achieved Full-cycle ROE Target Note: Includes Non-GAAP Financial Measures, such as ROE and EBT % of Operating Revenue. Please see Appendix – Non-GAAP Financial Measures for the reconciliation to the GAAP Financial Measure. KEY DRIVERS • De-risked the business and exited liability coverage lines • Exited United Kingdom • Accelerated SCS / DTS growth, including acquisitions • Upgraded lease pricing model • $100M+ annual maintenance savings • Achieved ~80% of pricing initiatives in 2023 $191 $352 2018 2019 2020 2021 2022 20232018 2023 8% 13%

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS A Resilient, Diversified, and Higher-performing Business 87 More Resilient Model Set to Deliver Long-term Value Note: Includes Non-GAAP Financial Measures, such as ROE and Comparable EPS. Please see Appendix – Non-GAAP Financial Measures for the reconciliation to the GAAP Financial Measure. FOCUS ON OPERATIONAL EXCELLENCE YIELDS SIGNIFICANT RESULTS Capitalize on secular trends Higher recurring revenue Investment in growth Organic growth in all 3 segments and strategic M&A Maintenance initiatives $100M+ of annual savings Pricing discipline Lease returns less reliant on used vehicle proceeds Operational efficiencies Improved operating leverage Maintain disciplined capital allocation Increased ROE 2018 2023 FMS SCS DTS $8.4 $11.8 16% 29% 56% 44% 41% 15% TOTAL REVENUE ($B) 2018 2023 $5.95 $12.95 COMPARABLE EPS Revenue growth across all three segments 17% CAGR 7% CAGR Execution on margin expansion initiatives and growth

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS STRATEGIC BENEFITS • Mostly long-term leases of 4 to 7 years • De-risked pricing through lower residual value estimates • Differentiated and segmented lease portfolio by application • Consistently achieving targeted spread (100-150 bps) over cost of capital • Improved asset mix by growing in less volatile asset classes • Achievement of multi-year maintenance initiatives Raised Returns by Upgrading Lease Portfolio 88 Strengthened Portfolio Performance Supports ChoiceLease Capital Investment CHOICELEASE MARGIN Execution on ChoiceLease margin expansion and growth initiatives 2018 2023 28% +19% +3% ChoiceLease Revenue ChoiceLease Fleet Current Performance and Market Conditions Achieving outstanding operational and investment performance Higher new vehicle prices continue to provide strong support for lease rates Future technology change creating incremental leasing demand 1 1 2018 excludes results related to FMS U.K. business, which we exited in 2023.

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS MARKET ASSUMPTIONS • Muted macroeconomic growth • Freight conditions expected to gradually improve in 2H24 • Secular trends continue to favor outsourcing • Class 8 U.S. tractor production down 25%; continued OEM delivery delays for trucks • Gains from used vehicles expected to be at normalized levels • Rental utilization expected to be below target range on smaller average fleet Reaffirming 2024 Outlook 89 2Q 2024 Outlook on Track; Confident in Full-year 2024 Outlook Note: Includes Non-GAAP Financial Measures, such as Operating Revenue, Comparable EPS, ROE, and Free Cash Flow. Please see Appendix – Non-GAAP Financial Measures for the reconciliation to the GAAP Financial Measure. ~10% $11.75 - $12.50 15.5% - 16.5% $(175) - $(275)M 2024 FORECAST Operating Revenue Growth Comparable EPS ROE Free Cash Flow

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Downside Risk Low as We Approach Expected End of Freight Recession 90 1 Illustrative for Truck and Tractor (U.S. only) fleets. Depicts Ryder's sales prices as a percent of original cost indexed to the value in 1999 to show the percent change in value each year. Excludes vehicles operated in excessively high mileage applications and sales prices adjusted to a consistent age at sale. Sales prices incorporate retail/wholesale mix at the respective time periods. Expect to Deliver Full Year UVS Gains in 2024 at Normalized Levels of $75M to $100M Historical Sales Price as % of Original Cost and Current Residual Value Estimates TRUCK RESIDUAL INDEX1 TRACTOR RESIDUAL INDEX1 ACCOUNTING RESIDUALS • Previously lowered by ~30% to address used vehicle volatility risk and incorporated a tractor downturn into estimates USED VEHICLE GAINS • Pricing expected to trough in middle of 2024 with gradual recovery in 2H’24 • Expect elevated vehicle proceeds beginning in 2026 and into 2027 from upcoming technology changes 25 45 65 85 105 125 145 165 185 1999 2001 2004 2006 2009 2011 2014 2016 2019 2021 2024 Residual Estimate for Accounting 25 45 65 85 105 125 145 165 185 1999 2001 2004 2006 2009 2011 2014 2016 2019 2021 2024 Residual Estimate for Accounting

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS -5% 0% 5% 10% 15% 20% 25% 30% CLEAR PATH TO ACHIEVE HIGHER RETURNS • New multi-year maintenance cost- savings initiative • Incremental benefits from enhanced pricing of new and renewed leases • Profitable contractual growth – lease, dedicated, and supply chain • Realization of acquisition synergies and improved operating efficiency • Asset management playbook Raising ROE Target to Low 20s Over Freight Cycle Structural Changes Are Driving Higher Highs and Higher Lows Note: Includes Non-GAAP Financial Measures, such as ROE. Please see Appendix – Non-GAAP Financial Measures for the reconciliation to the GAAP Financial Measure. Note: Record 2022 ROE reflects outsized gains from used vehicle sales and rental performance. 91 2013 2014 2015 2016 2017 2018 2019 2020 2021 2022 2023 2024F ROE Target Over Cycle NEW TARGET Low Twenties PRE-TRANSFORMATION Mid Teens PRIOR TARGET High Teens Future

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Strong Visibility to Higher Returns 92 Ongoing Execution of Strategy Lifting Returns Profile +300bps ROE ROE Prior Target Over the Cycle High Teens New Target Over the Cycle FMS New maintenance initiative, lease pricing, growth SCS / DTS e-Comm and RLM optimization, acquisition synergies, flex operating structure, growth Low Twenties +300 bps ROE Note: Includes Non-GAAP Financial Measures, such as ROE. Please see Appendix – Non-GAAP Financial Measures for the reconciliation to the GAAP Financial Measure.

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Favorably Positioned for Cycle Upturn 93 Execution through Cycle Upturn Expected to Add Significant Incremental Benefits at Next Cycle Peak UPTURN CONDITIONS KEY OPPORTUNITIES EXPECTED ANNUAL BENEFIT BY PEAK FMS Improved freight market • Grow rental fleet to capitalize on increased demand • UVS gains above normalized levels Pre-buy activity ahead of 2027 EPA engine technology change • Higher ChoiceLease sales • Higher UVS proceeds (2026+) DTS Tightening of driver market • Additional sales opportunities SCS Recovery of Omnichannel retail • Leverage expanded footprint

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Higher Returns and Strong Balance Sheet Provides Flexibility and Ample Investment Capacity Earnings Power Expected to Create Capacity to Grow Further 94 1 Debt capacity based on 2.75x leverage. Invest in Growth • Invest in our business at attractive returns – lease and rental fleet growth – Cost discipline and sustained lease pricing expected to increase cash generation • Ample capacity for value-added M&A Return Capital to Shareholders • Dividend growth aligned to earnings growth • Remain opportunistic as a means to return capital to shareholders $13B - $14B UVS Proceeds ~$2.0B Cash from Operations $7.5B – $8.5B Incremental Debt Capacity ~$3.5B Sources Dividends ~$0.4B Replacement CapEx ~$8.8B Cumulative Deployable Cash Uses 2024F-2026F CAPITAL DEPLOYMENT CAPACITY1 $3.8B – $4.8B

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Strong Fundamentals Against Peers 16% 3% 3% EBT 5-year CAGR1 20% 11% 14% ROE1 9.7x 15.6x 20.8x NTM P/E Ryder S&P 400 TransportationS&P 400 Value Note: 5-year defined as 2018-2023. ROE and NTM P/E as of 12/31/2023. Peer data represents median values for S&P 400 Value and S&P 400 Transportation indices. Metrics presented as defined by CapIQ unless otherwise noted and may differ from company-reported amounts. 1 2023 CapIQ data for Ryder adjusted to exclude the impact from the cumulative currency translation charge associated with the exit of the UK ($188M EBT). 95 7% 6% 5% Revenue 5-year CAGR 23% 13% 20% TSR 5-year Average Annualized All data based on information sourced from CapIQ

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Financial Key Takeaways 96 Above-market returns delivered to shareholders reflecting strategy execution Outperformance expected to accelerate based on enhanced quality of contractual portfolio and benefits from cycle upturn Increasing long-term ROE target 01 02 03 Robust balance sheet capacity to invest in growth and return capital to shareholders 04 Note: Includes Non-GAAP Financial Measures, such as ROE. Please see Appendix – Non-GAAP Financial Measures for the reconciliation to the GAAP Financial Measure.

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Ryder Next Horizon: Invest with Us ROBERT SANCHEZ Chairman & Chief Executive Officer 97

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Why Invest in Ryder Targets defined as: High Teens - 17% to 19%, Low Twenties - 20% to 22%, LDD - 10% to 12%, Low Teens - 13% to 14%. HSD: High-Single-Digit. MSD: Mid-Single-Digit. LDD: Low-Double-Digit. Note: Includes Non-GAAP Financial Measures, such as ROE, Operating Revenue, and EBT % of Operating Revenue. Please see Appendix – Non-GAAP Financial Measures for the reconciliation to the GAAP Financial Measure. Industry leader driving outperformance through the cycle with complementary portfolio addressing customers' needs 01 Achieved significant transformative milestones reflecting execution of balanced growth strategy 02 Next phase of strategy focused on accelerating profitable growth supported by operational excellence and customer-centric innovation 03 Transformed business model and strategic initiatives support increased long-term Adjusted ROE (ROE) target 04 ROE Low Twenties Operating Revenue Growth Total Ryder HSD Fleet Management MSD Supply Chain LDD Dedicated HSD EBT as % of Operating Revenue Fleet Management Low Teens Supply Chain HSD Dedicated HSD Leverage (Debt-to-equity) 2.5x – 3.0x NEW TARGETS 98

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Q&A Session 99

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Solutions Showcase RyderShare E.J. Smith Group Director FMS Technology: RyderGyde & RyderElectric+ Jason Leon VP, Chief Technology & Product Officer Baton, A Ryder Technology Lab Andrew Berberick VP, Chief Product & Technology Officer Nate Robert VP, Chief Product & Technology Officer Expanded SCS Capabilities Darin Cooprider SVP, Consumer Packaged Goods Warehouse Automation & Technology Gary Allen VP, Supply Chain Excellence Nearshoring Ricardo Alvarez VP & Managing Director – Ryder Mexico Tom Regan SVP, Automotive, Aerospace, & Industrial 100

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Appendix 101

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Non-GAAP Reconciliations 102

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Comparable EPS Reconciliation 103 Full Year 2018 Full Year 2022 Full Year 2023 Full Year 2024 Forecast EPS from continuing operations (GAAP) $5.43 $16.96 $8.73 $10.95 – $11.70 Non-operating pension costs, net 0.09 0.14 0.68 0.74 Restructuring and other, net 0.08 – – – FMS U.K. exit – (1.61) (0.40) – Currency translation adjustment loss – – 3.93 – ERP implementation costs 0.01 – – – Goodwill Impairment 0.29 – – – Other, net – (0.02) 0.01 0.05 Tax adjustments, net 0.05 0.90 – – Comparable EPS from continuing operations (non-GAAP) $5.95 $16.37 $12.95 $11.75 – $12.50

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Adj. ROE Reconciliation1 1 Includes income taxes on other items impacting comparability. 2 Represents the impact of other items impacting comparability, net of tax, to equity for the respective period. 3 Non-GAAP elements of this calculation have been reconciled to the corresponding GAAP measures. A numerical reconciliation of net earnings to adjusted net earnings and average shareholders' equity to adjusted average total equity is provided on this slide. 104 ($M) 2013 2014 2015 2016 2017 2018 Net earnings $238 $218 $305 $263 $720 $285 Other items impacting comparability — 115 18 13 24 22 Tax impact1 (2) (44) (7) (5) (535) 2 Adjusted net earnings $236 $289 $315 $271 $209 $308 Average total shareholders’ equity $1,594 $1,926 $1,895 $2,053 $1,984 $2,493 Average adjustments to shareholders’ equity2 (2) 8 11 2 (99) (78) Adjusted average total equity $1,592 $1,934 $1,906 $2,055 $1,885 $2,415 Adjusted ROE3 15 % 15 % 17 % 13 % 11 % 13 %

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS ($M) 2019 2020 2021 2022 2023 2024 Forecast Net earnings $(24) $(122) $519 $867 $406 $495 Other items impacting comparability 38 90 (10) (83) 157 5 Tax impact1 (6) 3 7 46 8 (5) Adjusted net earnings $8 $(29) $516 $830 $571 $495 Average total shareholders’ equity $2,533 $2,257 $2,453 $2,845 $3,041 $3,100 Average adjustments to shareholders’ equity2 (15) 60 14 (12) (19) – Adjusted average total equity $2,548 $2,317 $2,467 $2,833 $3,022 $3,100 Adjusted ROE3 – % (1)% 21 % 29 % 19 % 16 % Adj. ROE Reconciliation1 (Cont’d) 1 Includes income taxes on other items impacting comparability. 2 Represents the impact of other items impacting comparability, net of tax, to equity for the respective period. 3 Non-GAAP elements of this calculation have been reconciled to the corresponding GAAP measures. A numerical reconciliation of net earnings to adjusted net earnings and average shareholders' equity to adjusted average total equity is provided on this slide. 105

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Revenue 2023 Omnichannel retail $1,207 Automotive 1,061 Consumer packaged goods 926 Industrial and other 431 SCS Operating Revenue1 3,625 Subcontracted Transportation and Fuel 1,250 SCS Total Revenue $4,875 Earnings Before Tax (EBT) SCS Earnings Before Tax $231 SCS EBT as a % of SCS Total Revenue 4.7 % SCS EBT as a % of SCS Operating Revenue1 6.4 % Supply Chain Solutions (SCS) Note: Amounts may not be additive due to rounding. 1 Non-GAAP financial measure. F U L L Y E A R ( $ M ) 106

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Dedicated Transportation Solutions (DTS) Note: Amounts may not be additive due to rounding. 1 Non-GAAP financial measure. 107 Revenue 2023 DTS Operating Revenue1 $1,298 Subcontracted Transportation and Fuel 487 DTS Total Revenue $1,785 Earnings Before Tax (EBT) SCS Earnings Before Tax $121 SCS EBT as a % of SCS Total Revenue 6.8 % SCS EBT as a % of SCS Operating Revenue1 9.3 % F U L L Y E A R ( $ M )

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Comparable Segment EBITDA Note: Amounts may not be additive due to rounding. Segment EBITDA excludes eliminations, unallocated CSS, intangible amortization expense, non-operating pension costs, net and certain other. 1 Excludes the impact of depreciation and gains on vehicles sold allocated to SCS and DTS. 2 Non-GAAP financial measure. A reconciliation of GAAP net earnings to comparable EBITDA for each business segment (FMS, SCS and DTS) is set forth in this table. 108 F O U R T H Q U A R T E R ( $ M ) 2023 YTD SCS DTS Earnings before income tax $231 $121 Interest expense / (income) 8 (3) Depreciation1 136 3 Used vehicle sales, net1 — — Comparable Segment EBITDA2 $375 $121

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Fleet Management Solutions (FMS) NM: Not Meaningful. Note: Amounts may not be additive due to rounding. 1 Non-GAAP financial measure. 2 Includes intercompany fuel sales from FMS to SCS and DTS. 3 2018 not restated for amortization. Revenue 2023 2018 ChoiceLease $3,181 $2,832 Commercial Rental 1,178 961 SelectCare and other 694 590 FMS Europe — — FMS Operating Revenue1 5,053 4,383 Fuel Services Revenue2 877 876 FMS Total Revenue $5,930 $5,259 Earnings Before Tax (EBT)3 FMS Earnings Before Tax $665 $340 FMS EBT as a % of FMS Total Revenue 11.2 % 6.5 % FMS EBT as a % of FMS Operating Revenue1 13.2 % 7.8 % 109 F U L L Y E A R ( $ M )

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Operating Revenue Growth Note: Amounts may not be additive due to rounding. 1 Non-GAAP financial measure. 110 2 0 2 4 O P E R A T I N G R E V E N U E G R O W T H R E C O N C I L I A T I O N ($M) 2024 Forecast 2023 Change Total Revenue $13,000 $11,783 10% Subcontracted Transportation and Fuel (2,600) (2,286) 14% Operating Revenue1 $10,400 $9,497 10% ($M) 2023 2022 Change Total Revenue $11,783 $12,011 (2) % Subcontracted Transportation and Fuel (2,286) (2,731) (16) % Operating Revenue1 $9,497 $9,280 2 % 2 0 2 3 O P E R A T I N G R E V E N U E G R O W T H R E C O N C I L I A T I O N

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Cash Flow Reconciliation Note: Amounts may not be additive due to rounding. 1 Included in cash flows from investing activities. 2 Non-GAAP financial measure. 3 We calculate free cash flow as the sum of net cash provided by operating activities, net cash provided by the sale of revenue earning equipment and operating property and equipment, and other cash inflows from investing activities, less purchases of property and revenue earning equipment. 111 ($M) 2023 2024 Forecast Net Cash Provided by Operating Activities from Continuing Operations $2,353 $2,400 Proceeds from Sales (Primarily Revenue Earning Equipment)1 827 600 Other, net1 – – Total Cash Generated2 3,180 3,000 Purchases of Property and Revenue Earning Equipment1 (3,234) (3,225) Free Cash Flow2,3 $(54) $(225)

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Speaker Bios 112

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Robert Sanchez Chairman & CEO Robert E. Sanchez is chairman and chief executive officer of Ryder System, Inc. (NYSE: R), a leading supply chain, dedicated transportation, and commercial fleet management solutions company. He was named CEO in January 2013 and chairman of the board in May 2013. Over the course of more than 30 years at Ryder, Mr. Sanchez has held many senior executive leadership positions including president and chief operating officer (COO), chief financial officer (CFO), president of Fleet Management Solutions (FMS), chief information officer (CIO), SVP of transportation management within Supply Chain Solutions (SCS), and VP of asset management. He has been a member of the company’s executive leadership team since 2003. In his earlier roles, Mr. Sanchez played a key part in implementing the strategy to centralize Ryder’s asset management function and improve its cost management which drove an improvement in the return on capital and earnings of the company. As CEO, he has led the development and execution of Ryder’s growth strategy focused on the large segment of businesses that do not yet outsource their fleet management and supply chain functions. Before joining Ryder, Mr. Sanchez held engineering positions at Pratt & Whitney Aircraft and Florida Power & Light. Mr. Sanchez is on the Board of Directors of Texas Instruments. He also serves on the Board of Directors of the United Way Miami (immediate past chairman of the board), Foundation for Human Rights in Cuba, and Association of Cuban American Engineers (ACAE). He is also a member of the Board of Trustees of the University of Miami and St. Thomas University. Mr. Sanchez earned his MBA from The Wharton School at the University of Pennsylvania with a concentration in Finance and Strategic Management and a Bachelor of Science degree in Electrical Engineering from the University of Miami. 113

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Karen Jones is executive vice president, chief marketing officer (CMO), and head of new product development for Ryder System, Inc., a leading supply chain, dedicated transportation, and commercial fleet management solutions company, and a member of Ryder’s executive leadership team. As CMO, she is responsible for integrating the management of all marketing and brand-related activities across Ryder to drive growth and enhance brand value. Responsible for driving growth and ever-better customer experiences, Ms. Jones also leads new product innovation with a focus on technologies tackling supply chain disruptions driven by accelerating demand for next-generation vehicles, e-commerce fulfillment, commercial asset sharing, and digital technologies. She also heads up Ryder’s $50 million corporate venture capital fund RyderVentures, which invests in and partners with start- up companies to help speed to market emerging supply chain and transportation technologies. Prior to joining Ryder, Ms. Jones was CMO for NRG/Reliant Energy, Inc., where she was responsible for launching the company’s new corporate brand in 2010. Prior to that, she served as senior vice president of marketing and corporate communications for DHL Express in the United States. Her marketing efforts at DHL resulted in the largest awareness increases in the company’s history and within the logistics category, which were considered a major contributor to the advancement of DHL’s recognition in the “Top 100 Most Valuable Brands” by BrandZ. Prior to DHL, Ms. Jones served in positions responsible for worldwide brand advertising, sponsorship, strategic alliances, and product marketing for Hewlett Packard and Compaq Computer Corporation. Ms. Jones’ achievements have earned her multiple awards and recognitions during her career including being named a recipient of Supply & Demand Chain Executive’s “Women in Supply Chain” award in 2022 honoring female supply chain leaders whose accomplishments, mentorship, and examples set a foundation for women in all levels of a company’s supply chain network. Ms. Jones serves on the executive board of trustees for Ultimate Medical Academy (UMA) and the Boothbay Harbor Memorial Library Foundation. Ms. Jones holds a B.A. in Journalism from the University of Houston. Karen Jones EVP, CMO, & Head of New Product Development 114

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Steve Sensing is president of Supply Chain Solutions (SCS) and Dedicated Transportation Solutions (DTS) at Ryder System, Inc., a leading supply chain, dedicated transportation, and fleet management solutions company. In this role, Mr. Sensing is responsible for the management, operations, sales, and financial performance of Ryder’s SCS and DTS businesses leading a network of drivers, vehicles, distribution, transportation, e-commerce, and warehouse operations, as well as a shared network of e-fulfillment and “big and bulky” last mile locations dedicated to specific customers. He is a member of Ryder’s executive leadership team. Previously, Mr. Sensing served as the vice president and general manager of the Technology and Healthcare industry groups for Ryder SCS. He worked with customers in the electronics, telecommunications, medical, technology, and appliance manufacturing industries, and his responsibilities included strategic planning, developing new products and services, and leading tactical execution for global operations. With a Ryder career spanning more than 30 years, Mr. Sensing joined the company in 1992 as general manager leading the operations of Dedicated Contract Carriage solutions for regional accounts. He subsequently served in a variety of positions of increasing responsibility, including group manager for Ryder Dedicated; director of customer Logistics Distribution Management; and group director of operations for Ryder Integrated Supply Chain Solutions. His experience includes overseeing the network design and operation of Ryder solutions in dedicated transportation, transportation management, network optimization, distribution management, sales, operations, engineering, LEAN, and IT. Before joining Ryder, Mr. Sensing served as transportation manager for Trans Fleet Enterprises/Northern Telecom, where he was responsible for managing private fleet operations in the United States. Mr. Sensing earned his Bachelor of Science degree in Business Administration from the University of Tennessee in Knoxville, where he majored in Logistics and Transportation. He also completed the Executive Development Program at the University of Pennsylvania’s Wharton School in 2013, and a strategic innovation session at Vanderbilt University’s Owen Graduate School of Management. Mr. Sensing is a member of the advisory board for the Global Supply Chain Institute at the University of Tennessee’s Haslam College of Business. Steve Sensing President, SCS & DTS 115

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Steve W. Martin is executive vice president of Dedicated Transportation Solutions (DTS) for Ryder System, Inc., a leading supply chain, dedicated transportation, and fleet management solutions company. In this role, Mr. Martin is responsible for the strategic direction, customer satisfaction, growth, and business results of Ryder’s DTS business segment, which is a network of drivers, vehicles, and operations all dedicated to specific customers. Mr. Martin also heads up Ryder’s managed transportation and freight brokerage services. He is a member of Ryder’s executive leadership team. Most recently, Mr. Martin served as senior vice president of the DTS business unit. Prior to this role, he was vice president and general manager of the Automotive, Aerospace & Industrials segment within Ryder’s Supply Chain Solutions (SCS) business where he led teams providing supply chain management for original equipment manufacturers, their supplier and distribution base, as well as a broad range of manufacturing companies. Mr. Martin joined Ryder in 1988 as operations supervisor, supporting the Automotive industry group, and later advanced through the organization to positions of increasing responsibility, both domestically and abroad, leading engineering, quality assurance, and functional teams to support Ryder’s customers in the SCS and DTS business segments. Mr. Martin earned a Bachelor of Science degree in Transportation & Logistics from the University of Tennessee in Knoxville. He completed an executive leadership program at The Wharton School of the University of Pennsylvania and an executive education series on Negotiations & Decision-Making at Harvard Business School. Mr. Martin is an active member of the American Trucking Association (ATA), the largest national trade association for the trucking industry. Steve Martin EVP, DTS 116

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS Tom Havens is president of Fleet Management Solutions (FMS) for Ryder System, Inc., a leading supply chain, dedicated transportation, and fleet management solutions company. In this role, Mr. Havens leads all areas of business operations for the company's FMS business providing full-service leasing, contract maintenance, as well as commercial rental of trucks, tractors, and trailers to customers of all sizes and industries. Mr. Havens is a member of Ryder’s executive leadership team. A more than 30-year veteran of Ryder, prior to his current role, Mr. Havens was senior vice president and global chief of operations for the FMS business unit, a role he held for nearly nine years. Previously, Mr. Havens served as vice president and general manager for FMS in Canada, where he was responsible for developing the country strategy, providing leadership direction for operations, sales, rental and asset management, and financial planning and forecasting. Mr. Havens joined Ryder in 1993 as a rental representative in San Diego. Throughout his tenure with Ryder, he has held a variety of positions of increasing responsibility and various functions, including a rental manager for many locations, asset manager for the west region, general manager for San Francisco, vice president of asset management and vehicle sales, as well as head of operations for Ryder’s west region. He earned his MBA in International Business from San Diego State University and a Bachelor of Arts degree in Economics from the University of Rochester. Tom Havens President, FMS 117

RYDER 2024 INVESTOR DAY // SUPPLY CHAIN | DEDICATED TRANSPORTATION | FLEET MANAGEMENT SOLUTIONS John Diez is executive vice president and chief financial officer (CFO) for Ryder System, Inc., a leading supply chain, dedicated transportation, and fleet management solutions company. He is responsible for Ryder’s financial management functions, including finance and accounting, treasury, tax, audit, corporate strategy, and investor relations. He is a member of Ryder’s executive leadership team. Most recently, Mr. Diez served as president of Ryder’s Fleet Management Solutions (FMS) business unit. He led all areas of global fleet operations, which included providing full-service leasing, contract maintenance, as well as commercial rental of trucks, tractors, and trailers to customers across a variety of industries. Prior to this role, Mr. Diez was president of Ryder’s Dedicated Transportation Solutions (DTS) business unit where he was responsible for setting the strategic direction of DTS, which combines vehicles, drivers, and administrative services with drivers and additional value-added services, all dedicated to a specific customer. Mr. Diez joined the company in 2002 and has held various senior leadership operating and finance roles at Ryder. Before joining Ryder, Mr. Diez started his career in the audit practice of KPMG LLP. Mr. Diez is a member of the Board of Directors for Trinity Industries, Inc. (NYSE: TRN). He also serves on the Board of Directors of the U.S. Chamber of Commerce, Jackson Health Foundation, and United Way Miami. A licensed Certified Public Accountant (CPA), Mr. Diez earned both his Bachelor of Science and Master of Science in Accounting from Florida International University. John Diez EVP & CFO 118