Roughly 3.3 million veterans who qualify for VA healthcare have never enrolled, according to estimates from veterans’ advocacy organizations — many of them unaware the benefit applies to them at all. Sheila LaRoche, 37, was one of them until a support group meeting in January 2026 changed the equation.
I first connected with Sheila after a veterans’ support group based in Chicago’s Logan Square neighborhood forwarded her name to me. She had described her situation at one of their monthly meetings, and the group coordinator told me her story was “one we hear more than you’d think.” When I sat down with Sheila at a coffee shop on Milwaukee Avenue a week later, she arrived with a folder thick with documents she’d spent several evenings organizing — insurance renewal notices, printed VA web pages, and a receipt she clearly wasn’t happy about.
Sheila has worked as a dental assistant at a private practice in Chicago’s Wicker Park neighborhood since 2019. She served four years in the U.S. Army, leaving in 2015 after completing her service contract. Her income — approximately $68,000 annually — places her solidly in the upper-middle range for a single person with no dependents. She shares an apartment with a roommate to manage rent in a city where one-bedroom units regularly exceed $1,800 per month. On paper, Sheila looks like someone who doesn’t need help. The reality she described was more complicated than that.
When the Renewal Notice Arrived
The breaking point came in October 2025, when Sheila received her annual health plan renewal notice from her individual marketplace insurer. The number she saw stopped her cold.
“I had been paying $382 a month,” she told me, spreading the renewal paperwork across the table. “The new premium was $764. I made a noise — I don’t even know what kind of noise — and my roommate came in to check on me.”
Her employer, a small private dental practice with fewer than ten employees, offers no group health coverage. Sheila has bought her own individual plan through the marketplace since 2020. Prior year increases had been incremental — twenty or thirty dollars at a time. But the 2026 renewal represented a 100% increase in a single year, driven partly by a shift in her plan’s risk pool and a reduction in her subsidy eligibility tied to income level.
At $764 per month — $9,168 annually — health insurance alone consumed roughly 13.5% of Sheila’s gross income. She started looking for alternatives almost immediately. A coworker mentioned the VA. Sheila had heard that veterans could access healthcare through the Department of Veterans Affairs, but had always assumed her income made her ineligible, or that the benefit was reserved for combat veterans with documented injuries.
“I thought it was for guys who came back from war zones and got hurt,” she said. “I didn’t think about it as something that applied to me.”
The Veterans’ Benefits Maze — and a $178 Mistake
Sheila began researching VA healthcare enrollment on her own in November 2025. She found VA.gov useful but overwhelming — a tangle of eligibility tiers, priority groups, income thresholds, and service-connected versus non-service-connected care distinctions. She spent several evenings clicking through pages without arriving at a clear answer about what she actually qualified for.
In December, she encountered something that made things worse. A company advertising “VA claim optimization services” reached out after she joined an online veterans’ forum. They promised to accelerate her healthcare enrollment and assess her for a disability rating in exchange for a monthly fee of $89. She signed up.
She was right to be suspicious. According to The War Horse, the VA sent warning letters to numerous veteran disability benefit companies, raising concerns that some may be acting improperly in their handling of claims. And in February 2026, California became one of eleven states to ban private companies from charging fees to veterans for basic VA disability claim assistance, a law Governor Newsom signed after pressure from advocates who called these operations “claim sharks,” according to CalMatters.
Illinois does not yet have a law identical to California’s, but the principle holds nationally: accredited VSOs are free, and the VA itself has been increasing its scrutiny of for-profit claims intermediaries. Sheila’s $178 is money she describes as simply gone.
The Turning Point: One Group Meeting, One Volunteer
Sheila demanded a refund from the company and did not receive one. She found the Logan Square veterans’ support group in January 2026 through a Facebook post, largely out of frustration. It was there that she first heard, clearly and plainly, that free enrollment help existed through accredited VSOs.
A VSO volunteer met with her in early February and walked her through VA healthcare Priority Group enrollment. Because Sheila has no documented service-connected disability, she falls into Priority Group 7 — eligible for most VA services, with modest copays for certain care. For a single veteran in the Chicago metropolitan area with no dependents, her income placed her within the qualifying range for that group.
The VSO volunteer also helped Sheila access and download her VA benefit summary letters through the official VA records portal — a step she hadn’t known was possible. The VA has also recently launched a Claim Assist Portal, designed to give veterans a faster, more direct way to respond to open claim requests, according to VA News. Sheila told me she plans to use it if she pursues a disability rating evaluation in the coming months.
The Outcome — and What Remains Unresolved
By March 2026, Sheila had been approved for VA healthcare enrollment and had her first primary care appointment scheduled. She has not yet dropped her marketplace plan — she’s keeping it through the end of the plan year while she evaluates how VA coverage handles her specific needs, particularly dental and vision, which the VA covers under more limited circumstances for Priority Group 7 enrollees.
The math still isn’t entirely comfortable. She is currently paying both the $764 marketplace premium and preparing for VA copays of approximately $30 to $50 per primary care visit. Her goal is to transition fully to VA care by mid-2026, which she estimates would save her roughly $700 to $720 each month.
Sheila is also cautiously exploring whether she has any service-connected conditions that might qualify her for a disability rating, which could further reduce or eliminate VA copays and unlock additional state-level veteran benefits. According to Military.com’s 2026 state veterans’ benefits directory, Illinois offers property tax relief, employment resources, and additional benefits for veterans with qualifying disability ratings. Sheila is careful not to get ahead of herself.
“I’m trying to stay realistic,” she told me as we finished our coffee. “I’m not out of the woods. But I feel like I’m at least walking toward the exit now, instead of just standing there in the dark.”
The bitterness over the $178 she lost to the fee-based company hasn’t fully faded. When I asked if she’d reported them, she paused. “I filed a complaint with the VA,” she said. “Whether anything happens with it — I don’t know. But someone else shouldn’t have to learn what I learned the hard way.”
What stays with me from Sheila’s story isn’t the dollar amounts, though they’re real and significant. It’s the time — months of confusion, misdirection, and wasted money that might have been avoided if someone had clearly communicated, years earlier, that her service entitled her to something. The support group in Logan Square did in one evening what years of solo research had not. That gap — between what veterans are owed and what they actually know to claim — is the thing worth examining.
Related: He Showed Up to a Medicare Event With the Wrong Questions — and Left With a Plan That Saved His Family $4,200
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