Jackie James, Director, TIAA-CREF Tuition Financing, Inc. (TFI) Program Marketing
As someone who grew up in a military family, I have seen firsthand how military education benefits can transform lives across generations. Both of my grandfathers served our country. My dad retired as a Brigadier General from the US Air Force and the Air National Guard, and my brother is currently serving. Through their experiences, I’ve learned that veterans earn well-deserved educational benefits with the GI Bill. However, many do not realize how combining their GI Bill benefits with 529 college savings plans can create a powerful strategy for maximizing educational opportunities.
The GI Bill Foundation I Grew Up Understanding
Growing up, I watched my dad navigate his military education benefits. I learned how the Post-9/11 GI Bill provides funding for tuition and a monthly stipend for other expenses, such as housing, books, and supplies. 1 These benefits can be used for undergraduate degrees, graduate programs, vocational training, and certification programs. Although there are several different GI Bills, what makes the Post-9/11 GI Bill particularly valuable, and why my dad decided to use it, is its transferability feature – something my mom and dad discussed extensively as they considered how to support their children’s educational goals best.
My parents made the decision to transfer his GI Bill benefits to cover my and my brothers’ higher education expenses. Two of us attended an in-person 4-year college, while one pursued flight training and earned an online degree from a 4-year college. Thanks to his military benefits and his forward-thinking financial skills, we were all able to graduate with no debt – a tremendous gift that has shaped our financial futures.
The Post-9/11 GI Bill provides 36 months of education benefits – enough to cover a typical four-year degree when used efficiently. However, this creates an important planning consideration for military families, especially those with multiple children who could benefit from these educational resources. Once a veteran transfers or uses any portion of their 36-month benefit, those months are permanently expended, whether used by the veteran themselves or transferred to a spouse or child.1
This means families with multiple potential beneficiaries must make strategic decisions about how to allocate this valuable but limited resource. When GI Bill benefits are exhausted – whether after 36 months or when split among family members – any remaining educational expenses must be covered through savings, investments, personal funds, loans, or other financial aid.1
This is precisely where 529 college savings plans can become invaluable, providing a reliable funding source to bridge gaps when GI Bill benefits run out or to fund education for additional family members who may not receive transferred benefits.
How 529 Plans Can Enhance Military Benefits
Through my family’s planning process, I learned that a 529 plan can serve as the perfect partner to GI Bill benefits. These tax-advantaged college savings accounts allow families to save and invest for qualified education expenses, with earnings growing tax-deferred at both the federal and state levels, and withdrawals remain tax-free when used for qualified expenses.
My Mom and Dad celebrating my Dad’s retirement from the Air National Guard after 35+ years of service
529 plans can offer several strategic advantages. First, they can cover expenses that exceed the GI Bill limits, such as the difference between private school tuition and the maximum benefit amount. Second, 529 funds can pay for expenses beyond the 36-month allotment, helping families pay for multiple beneficiaries who want to further their education.2
Maximizing Both Benefits
Planning allows veterans to optimize both resources, something I’ve observed across three generations of military service in my family. Consider using GI Bill benefits for the most expensive educational goals – perhaps a child’s four-year degree at a state university where the benefit provides maximum coverage. Meanwhile, 529 plans can supplement these benefits or fund the education of additional family members.
Alternatively, since the GI Bill benefits do have a limit, consider using each month’s allotment strategically: apply the GI Bill toward a beneficiary pursuing more expensive degrees, while utilizing 529 plan savings to cover lower-cost options for other beneficiaries, such as technical programs, professional certifications, or apprenticeships.3
The recent SECURE Act 2.0 can add even more flexibility to 529 plans, allowing unused funds to be rolled over to a Roth IRA under certain conditions, providing a retirement savings alternative for military families who prioritize college savings.4
State-Specific Benefits
Many state 529 plans offer additional benefits for families. Some states provide matching contributions or tax deductions/credits for contributions made into a 529 plan. Prior to investing, Veterans should check with their current state of residence to learn if it offers tax or other benefits, such as financial aid, scholarship funds, or protection from creditors, for investing in its own 529 plan.
Getting Started: Advice from a Military Family
Veterans interested in maximizing their educational benefits should start by understanding their specific GI Bill entitlements and transfer options. Then, research a 529 plan and how different plans compare. Many financial advisors specialize in military benefits and can help create comprehensive strategies that optimize both the GI Bill and 529 plan advantages.
The combination of earned military benefits and strategic 529 plan savings can create powerful opportunities for veterans and their families. Having witnessed this across generations in my own family, I know that understanding how these programs work together can help ensure that military families make the most of every educational dollar available to them.
To all the veterans and active service members reading this – thank you for your service and may these educational benefits serve as a pathway to bright futures for you and your families.
About the Author
Jackie James has worked in the financial services and 529 industry since 2018 and currently serves as a Director at TIAA-CREF Tuition Financing, Inc. (TFI), a wholly-owned subsidiary of TIAA. TFI operates as the 529 Plan Program Manager for the States of California, Georgia, Illinois, Kansas, Michigan, Minnesota, Oklahoma, Washington, and Wisconsin. In her role, Jackie has successfully managed strategic programs and initiatives that consistently drive business growth, with expertise in developing and executing marketing plans for the Edvest 529 College Savings Plan and Bright Start 529 College Savings Plan. She holds two Bachelor’s degrees in Marketing and Entrepreneurship from the University of South Carolina, and a Master’s degree in Project Management from the University of Maryland Global Campus. Jackie resides in the Greater Asheville area with her husband and two cats, and is passionate about youth mental health, volunteering as a Volunteer for the Guide Dog Foundation for the Blind and currently serving as the Sustainability Action Membership Co-Lead at TIAA.
*Information up to date as of November 1, 2025, GI Bill policies may change in the future.
1 U.S. Department of Veterans Affairs, “Post-9/11 GI Bill” (https://www.va.gov/education/about-gi-bill-benefits/post-9-11/)
2Internal Revenue Service, “529 Plans: Questions and Answers” (https://www.irs.gov/newsroom/529-plans-questions-and-answers)
3Apprenticeship programs must be registered and certified with the Secretary of Labor under the National Apprenticeship Act.
4SECURE Act 2.0, Public Law 117-328 (2022)
Please read the Plan Description on www.tiaa.org/529 carefully prior to investing, for details on its investment objectives, risks, charges, and expenses, and whether your home state offers tax or other benefits such as financial aid, scholarship funds, or protection from creditors for investing in its own 529 plan. More information about municipal fund securities is available in the issuer’s Plan Description. Investments in the plan are neither insured nor guaranteed and there is the risk of investment loss. Consult your legal or tax professional for tax advice. TIAA-CREF Tuition Financing, Inc. (TFI) is the Plan Manager for several state 529 plans, and TIAA-CREF Individual & Institutional Services, LLC, Member FINRA, is the distributor and underwriter for those plans.
Funds rolled over to a Roth IRA can be withdrawn free from federal and Wisconsin income tax. If you are not a Wisconsin taxpayer, these withdrawals may include recapture of tax deduction and state income tax. Account Owners and Beneficiaries should consult with a qualified tax professional before rolling over funds from their 529 plan to contribute to a Roth IRA.
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