My $150,000 GI Bill Mistake

Despite all my best research and planning, I was still hoodwinked by the Department of Veterans’ Affairs (VA) into the Montgomery GI Bill.

The Montgomery GI Bill isn’t eligible for housing allowance, Yellow Ribbon program, nor transfer to dependents.

It also expires 10 years after separation.
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There is always that sinking feeling in my heart when trying to utilize my military benefits. It’s a feeling as though now that I’m out, it was always a mirage to lure me in, and then just when I feel confident, they claw the benefits back as if they were never there to begin with.

Accessing military benefits is a tricky game, full of arbitrary (often omitted) rules designed to make it difficult to access the benefits sold to you in exchange for joining. I get it, these benefits are expensive, so the fewer veterans can access them, the lower the cost to the tax payer. But free markets also greatly frown upon false advertising.

I had this dream and it’s a bit silly, but I’ve always wanted to attend a private university in-person. It’s this unbearable, annoying competitive streak in me. The practical streak in me didn’t even apply to any private universities after high school. I assumed I couldn’t afford them, or decided the student loans would be so unreasonable for a liberal arts degree anyway.

I attended a great public university in-person and then did the whole veteran-discounted online Maters program while active duty. So, I remain hungry for a proper academic immersion again now a decade since undergrad.

The plan, even when I was just applying to the military, was always to use my Post 9/11 GI Bill to go to a private school that participated in the Yellow Ribbon Program. For almost 10 years, that was the goal I was working toward. My Post 9/11 GI Bill was always my get-out-of-jail free card, my disappear-and-start-a-new-life card. Turns out it never existed for me at all. Little did I know the dream I carried with me on active duty was a mirage the whole time, evaporating the moment I tried to touch it.

How I Got Stuck with the Montgomery GI Bill by Mistake

Back in 2016 Officer Training School, a VA rep came to our class and made us sign a piece of paper choosing between the Post 9/11 GI Bill and the Montgomery GI Bill as our assigned education benefit. Except they said, if you chose the Post 9/11 GI Bill, this is irrevocable! You will never be eligible for the Montgomery GI Bill.

This “irrevocability” rule would be later overturned in Rudisill v. McDonough in 2024, but more on that in a future post.

If you elect the Montgomery GI Bill, however, they said, you can transfer your remaining months of eligibility to the Post 9/11 GI Bill at any time AND if you chose the Montgomery GI Bill, when you run out of benefits, you can apply for an additional 12 months of the Post 9/11 GI Bill. Optionality, as it was advertised, was my strategy. So I elected to start with the Montgomery while pursuing my Masters on active duty (you don’t get the BAH benefit of Post 9/11 while you’re on active duty anyway), then convert my remaining months to Post 9/11 upon separation.

In Washington, DC, the Post 9/11 housing allowance alone is a greater benefit than the full-time Montgomery GI Bill rate.

But it was not until I used about four months of Montgomery benefit for my online Masters while active until I realized it was an even more terrible GI Bill than I initially realized. I decided to save the rest for conversion to Post 9/11 for post-separation studies.

Except I would never be able to.

Without my knowledge, the VA had convinced me to irrevocably waive my Post 9/11 GI Bill benefit for my active duty service.

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I found this out on the phone with the VA GI Bill office while on break outside my office building in early 2024. I burst into tears, shouting, “I knew it! I knew they were going to screw me again!”

I felt hoodwinked. I was hoodwinked. Those carefully confusing rules to gate keep benefits had worked, and on me–someone obsessive about financially planning and veteran benefits.

Two people walking by asked me if I was okay. I’m sure it looked as though I just heard someone had died. In a way, it did feel that way. The future I envisioned–joining the military as my ticket to a private education–had died.

Now I am stuck with the Montgomery GI Bill–a GI Bill so underwhelming, it can barely cover base tuition for public in-state Virginia universities (if at all), let alone any living expenses. My Post 9/11 GI Bill Basic Allowance for Housing (BAH) rate for the Washington DC area ($2,679) is technically more than the entire Montgomery monthly allotment for full time students ($2,438)! Meaning, even if I had a full-ride to a school in my current area, the Post 9/11 GI Bill housing allowance alone would still be the greater benefit than the Montgomery.

Afterall, the Montgomery GI Bill was for peacetime U.S. Veterans; it was never meant to cover the cost of education, merely defer it. Why the DoD/VA even offers this GI Bill to fresh service members–most of whom now were not even alive on 9/11–is preposterous.

What it Actually Takes to Convert Montgomery into Post 9/11

You haven’t been able to convert your Montgomery straight to Post 9/11 GI Bill for any qualifying service since 2009 (U.S. Code Title 38, Section 3327). So, if your service was pre-2009, you may still be eligible to convert. But for me, seven year later–probably unwittingly–the VA reps at my Officer Training School were selling me a pipe dream.

In order to convert my remaining months of benefit to Post 9/11, I would have to separate, re-join, and serve an additional 90 days for 50% Post 9/11 eligibility and 36 months if I wanted 100% eligibility. In other words, I would have to start all over again and separately re-qualify for the Post 9/11.

Had I not used those measly $2,000 worth of Montgomery benefits, I may still be eligible for the Post 9/11 GI Bill.

Since I had already used some of my Montgomery, this reality would been true had I served 5 years, 15 years, or 25 years. If there’s no gap in service, it’s all only one period of qualifying service.

However, considering as a disabled Veteran I am no ineligible for concurrent VA and military pay, I would have to waive my tax-free VA disability pension for any active duty military service.

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This legislation is a powerful machine that most of the time appears utterly ignorant, sometimes ambivalent to what it’s capable of building or destroying. I suppose that makes sense. Policy and law are just pieces of paper anyway.

But this is why I started this blog, to share those gut-wrenching stories of empty promises to protect each other.

The Downsides of Montgomery GI Bill

I’ve missed out on perhaps $150,000+ of education benefit because a VA rep didn’t know to say, “…if you separate, rejoin, and serve three more years” at the end of “You can convert the Montgomery to the Post 9/11.”

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Importantly, the Montgomery isn’t eligible for a monthly housing allowance.

Nor is the Montgomery eligible for Yellow Ribbon program benefits, where some private schools waive the remaining tuition for Post 9/11 GI Bill Veteran students. By the way, you must have 100% Post 9/11 eligibility to qualify for Yellow Ribbon at all.

This doesn’t apply to me, but it’s worth noting the Montgomery also isn’t eligible for transfer to dependents.

Finally, to really rub my face in the dirt, the Montgomery expires 10 years after separation. So now if I want to pursue additional education with my earned military education benefits, I have to finish said program within the next 5.5 years.

U.S. Code Title 38 Section 3322 “Veterans’ Benefits”

There is a provision in U.S. code where you can’t use the same period of qualifying service to qualify for more than one benefit. So my 5 consecutive years of active duty make me eligible for one of the GI bills, and without knowing, I locked myself into the Montgomery.

Why were they even offering the Montgomery still in 2016? Any recently joined service members, what’s the GI Bill situation now? Drop me a line.

Title 38 §3322. Bar to duplication of educational assistance benefits

(a) In General.—An individual entitled to educational assistance under this chapter who is also eligible for educational assistance under chapter 30, 31, 32, or 35 of this title, chapter 107, 1606, or 1607 or section 510 of title 10, or the provisions of the Hostage Relief Act of 1980 (Public Law 96–449; 5 U.S.C. 5561 note) may not receive assistance under two or more such programs concurrently, but shall elect (in such form and manner as the Secretary may prescribe) under which chapter or provisions to receive educational assistance.

(h) Bar To Duplication of Eligibility Based on a Single Event or Period of Service.—

(1) Active-duty service.—An individual with qualifying service in the Armed Forces that establishes eligibility on the part of such individual for educational assistance under this chapter [33 Post 9/11 GI Bill], chapter 30 [Montgomery GI Bill] or 32 [Post-Vietnam Era Veterans’ Educational Assistance] of this title…shall elect (in such form and manner as the Secretary may prescribe) under which authority such service is to be credited.

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In other words, you are only eligible for one GI Bill for one period of service. Regardless of which one you choose, it’s irrevocable. For someone who simply served and separated, there is no such thing as conversion for any GI Bill.

Had I had this information on that day of Officer Training School, why on earth would I have elected the Montgomery GI Bill and waived eligibility for housing allowance, Yellow Ribbon Program, transfer to dependents, and a nonexistent expiration date? Absolutely absurd.

I don’t think those countless VA reps understood they were doling out bad advice. The legislation around VA education benefits is so confusing, so incredibly complex, not even the VA’s own staff–employed to advise Veterans on how to navigate benefits–can adequately decipher it. That’s the real problem.

What’s Next?

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I’m still a little raw, but I’m figuring it out. I remind myself time and time again, I was awarded the real benefit: the VA disability pension and VA healthcare by extension. I’ll be just fine. I’ve already opened a 529 education account and started researching programs in the National Capital Region.

Please, if you have any recommendations, send them my way!

With federal sector job opportunities as they are, I may very well have to retrain within the next few years regardless. I’ll just have to get crafty with the Montgomery.

At the end of the day, unlike in the military, nothing is guaranteed in exchange for your labor and loyalty: not housing, not healthcare, certainly not education, and not even the job you already have and are killing at. As a civilian in the capitalist marketplace, how hard you work and how loyal you are, are simply independent of shareholder value.

We must plan accordingly together.

How to Check Your Post 9/11 GI Bill Benefits

If you’re expecting Post 9/11 GI Bill benefits, you can double-check your eligibility by applying for Post 9/11 GI Bill benefits here: https://www.va.gov/education/how-to-apply/. You do not need to know what program to apply.

How to Check if Your Program is Even Eligible for GI Bill Benefits

Also don’t forget to double-check your desired education program is even eligible for GI Bill benefits by using the VA WEAMS Institution Search Tool.

One response to “My $150,000 GI Bill Mistake”

  1. Thank you for sharing your story. Hopefully the option to choose the Montgomery GI Bill goes away. I’m sure there are many many others who were mislead and they might not even know it if they aren’t doing their research. Extremely disappointed.

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