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Felix Grigori

Can a Sole Proprietor set up an HSA while covered by spouse's employer health insurance?

I've been running my own business as a sole proprietor for about 3 years now. My healthcare situation is that I'm covered under my wife's health insurance plan through her job. I've been trying to figure out if there's any way I can establish an HSA (Health Savings Account) to pay for medical expenses with pre-tax dollars. From what I've researched so far, it seems like I might be out of luck since I don't have my own qualifying high-deductible health plan (HDHP). Everything I've read suggests that to qualify for an HSA, you need to be enrolled in an HDHP yourself, not just as a dependent on someone else's plan. Is there any loophole or exception I'm missing here? Are there any other tax-advantaged options for healthcare expenses for someone in my situation? I'd really like to find a way to use pre-tax dollars for medical costs since I'm paying everything with post-tax income right now. Any advice would be greatly appreciated!

Felicity Bud

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You're mostly on the right track, but there's a bit more nuance to this situation. The key isn't whether YOU have the insurance, but whether the plan itself is HSA-eligible. If your wife's employer plan is a qualified High Deductible Health Plan (HDHP) that meets the IRS requirements for HSA eligibility, and you're covered under that plan, you can potentially contribute to an HSA. For 2025, those requirements include a minimum deduction of $1,600 for individual coverage or $3,200 for family coverage. The catch is that the HSA would technically be your wife's account since she's the primary policyholder, but HSA funds can be used for qualified medical expenses for any family member covered under the HDHP, including you. So while you couldn't establish your own HSA directly, you could benefit from one established through your wife's plan. If her employer plan isn't an HDHP, then unfortunately you're correct - there's no way to utilize an HSA in your situation. You might want to look into a Health FSA (Flexible Spending Account) through your wife's employer as an alternative, though this has lower contribution limits and different rules.

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Felix Grigori

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Thanks for the clarification. Her plan is definitely not a HDHP - it's a pretty comprehensive PPO with a relatively low deductible. Are there any other options for someone like me to get tax advantages for healthcare expenses? I was hoping there might be something specifically for self-employed people.

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Felicity Bud

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Since her plan isn't an HDHP, you can't take advantage of an HSA. For self-employed individuals, you do have a couple of other options though. One major tax benefit is the self-employed health insurance deduction, which allows you to deduct 100% of health insurance premiums paid for yourself, your spouse, and dependents as an adjustment to income (not as an itemized deduction). This includes premiums you might be paying to your wife's employer for your portion of the coverage. Another option worth exploring is setting up a Qualified Small Employer Health Reimbursement Arrangement (QSEHRA) if you have any employees, though this gets complicated as a sole proprietor with no employees. Some self-employed people also set up an S-Corporation and become employees of their own company, which opens additional options, but that's a significant business structure change that needs careful consideration.

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Max Reyes

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I was in the exact same boat as you last year! I'm a freelance graphic designer and my husband's company provides our health insurance. I spent hours researching HSAs and was getting super frustrated until I found https://taxr.ai that helped me understand my options. They analyzed my situation and confirmed what the previous commenter said - I couldn't set up my own HSA since I wasn't covered by a qualifying high-deductible plan. BUT they showed me how to properly take the self-employed health insurance deduction for the portion of my husband's premium that covered me. They also identified several medical expenses I could deduct as itemized deductions that I was completely missing. Saved me over $1,200 in taxes last year! The cool thing was they explained everything in plain English instead of tax jargon. Might be worth checking out since your situation is pretty similar to what mine was.

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Does taxr.ai actually connect you with real tax pros or is it just like an AI chatbot thing? I've used TurboTax for years and they always seem confused by my 1099 income alongside my W-2 job.

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Adrian Connor

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I'm skeptical about these online services. How much did it end up costing you? Their website doesn't seem to list pricing up front which is always a red flag to me.

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Max Reyes

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They have actual tax professionals that review everything, not just AI. The AI part helps organize all your documents and identifies potential issues, but then real experts check everything and provide personalized advice. It's way more thorough than what I got with TurboTax because they actually understand self-employment situations. As for pricing, I can't remember the exact amount but it was reasonable for what I got back in tax savings. They do a free initial analysis that shows you potential savings before you commit to anything. For me it was worth it just to have confidence that I wasn't missing any deductions related to my business and healthcare expenses.

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Just wanted to follow up - I checked out https://taxr.ai after seeing this thread and it was actually super helpful! My situation was similar (self-employed consultant with insurance through spouse) and they identified that I could take the self-employed health insurance deduction for the portion of premiums that covered me, even though my wife pays them from her paycheck. They also pointed out some home office deductions I was missing and helped me understand how to properly document business expenses that overlap with personal use. Just filed my taxes and ended up with about $3,800 more in deductions than last year. Definitely worth checking out if you're self-employed with a complicated insurance situation!

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Aisha Jackson

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Hey there, I know this is a bit off-topic from the HSA question, but have you tried calling the IRS directly to ask about your options? I did that last year when I had a similar question about my LLC and health insurance, and after 3 WEEKS of trying to get through, I found this service called https://claimyr.com that got me connected to an IRS agent in about 15 minutes. You can see how it works here: https://youtu.be/_kiP6q8DX5c The IRS agent I spoke with actually pointed me to some specific tax code rules for self-employed people that my accountant had missed. Turns out I could deduct a portion of my health expenses in a way I hadn't considered before. Might be worth a call to get the official word directly from them!

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Wait, how does this Claimyr thing actually work? Does it just keep calling the IRS for you or something? I've literally spent hours on hold with them before.

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Lilly Curtis

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Sorry but this sounds sketchy AF. The IRS would never let some third party service jump the phone queue. And why would anyone pay for something like this when you can just call yourself for free?

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Aisha Jackson

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It basically automates the calling process and navigates the phone tree for you. When it reaches an agent, it calls your phone and connects you directly to them. It saved me literally hours of waiting on hold and trying to get through their busy signals. It's not jumping any queue - it's just persistent with the calling when you don't have time to sit on hold all day. And to be honest, after trying for weeks to reach someone at the IRS myself and failing, the cost was 100% worth it to finally get definitive answers about my tax situation. Sometimes your time is more valuable than the service cost.

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Lilly Curtis

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I have to admit I was wrong about Claimyr. After seeing these responses, I decided to give it a try since I've been trying to reach the IRS about an issue with my self-employment taxes for almost a month. The service actually worked exactly as described - got me through to an agent in about 20 minutes after I'd previously spent hours and hours on hold without ever reaching a human. The agent was able to answer my questions about health insurance deductions as a sole proprietor and confirmed that while I can't have my own HSA without an HDHP, I can deduct a portion of my health insurance premiums. For anyone in a similar situation as the original poster - definitely worth getting clarification directly from the IRS since self-employment tax situations can get complicated quickly.

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Leo Simmons

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Just throwing this out there - have you considered talking to your wife's HR department about whether they offer an FSA (Flexible Spending Account)? It's not as good as an HSA since the money is use-it-or-lose-it each year, but you can still put pre-tax dollars in there for healthcare expenses. My husband is self-employed and I carry our insurance through my employer. We max out my FSA every year ($3,200 for 2025) and use it for all our family medical expenses. Not as good as the investment potential of an HSA, but still a decent tax savings.

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Felix Grigori

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That's a really good point - I hadn't thought about an FSA. I'll definitely ask her to check with HR about that option. Do you know if we'd still be eligible if we file taxes separately? And is there any special documentation needed to use the FSA for my expenses even though she's the one with the employer plan?

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Leo Simmons

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FSA eligibility doesn't depend on your tax filing status, so you're good whether you file jointly or separately. The FSA follows the health plan, so if you're covered under her insurance, your medical expenses qualify for FSA reimbursement with no special documentation beyond what's normally required (receipts, etc.). The main downside compared to HSAs is the "use it or lose it" feature, though many plans offer a $610 rollover or a 2.5 month grace period. We just make sure to schedule any needed medical/dental work toward the end of the year if we have funds left over. Another option that MIGHT work for you is looking into an Individual Coverage HRA (ICHRA) if you have any employees or are considering hiring any. But the FSA is probably your simplest option.

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Lindsey Fry

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Don't forget to look into whether you qualify for the self-employed health insurance deduction! Even though your wife's employer provides the insurance, if you're paying any portion of the premiums (either directly or indirectly by reimbursing your wife), you may be able to deduct that amount on your Schedule C. I'm in a similar situation and was able to deduct about 40% of our family premium last year because that was determined to be "my portion" of the coverage. Talk to a tax professional about how to calculate and document this properly.

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Saleem Vaziri

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Is this actually legit? I thought you couldn't deduct premiums if you're eligible for coverage through your spouse's employer plan? My accountant told me this wasn't allowed.

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Sofia Price

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@Saleem Vaziri Your accountant might be thinking of the rule that prevents you from deducting premiums if you re'eligible to participate in a subsidized health plan through your spouse s'employer. But the key word is subsidized. "If" you re'paying the full cost of adding yourself to your spouse s'plan meaning (the employer isn t'contributing toward your portion ,)then you can potentially deduct that amount as a self-employed person. The IRS allows self-employed individuals to deduct health insurance premiums paid for themselves and their families, even if the insurance is obtained through a spouse s'employer, as long as the premiums aren t'being subsidized by that employer for the self-employed person s'coverage. You ll'want to get documentation from your wife s'HR department showing exactly how much of the premium is allocated to your coverage versus hers. This can get tricky to calculate, but it s'definitely worth exploring with a tax professional who understands self-employment rules.

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I've been following this thread closely since I'm in an almost identical situation - sole proprietor with coverage through my spouse's employer plan. Just wanted to add a few things that might help: First, definitely pursue the FSA option that Leo mentioned. We've been using one for three years now and it's been great for predictable expenses like glasses, dental work, and prescriptions. The key is to be conservative with your contribution since you can't roll over much to the next year. Second, on the self-employed health insurance deduction - this is real but requires careful documentation. You'll need a letter from your wife's HR department breaking down the premium allocation. In our case, the employer contributes $200/month toward employee-only coverage, but we pay an additional $450/month to add me and our kids. I can deduct a portion of that $450 as a self-employed person. One thing I haven't seen mentioned is that you can also deduct qualified medical expenses as business expenses if they're directly related to your work. For example, if you need ergonomic equipment for your home office due to a medical condition, that could be deductible. Obviously consult a tax pro for specifics. The bottom line is that while you can't get an HSA in your situation, there are still several ways to get tax advantages for healthcare costs as a self-employed person. It's worth spending some time (or money on professional advice) to make sure you're maximizing all available options.

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This is incredibly helpful, Oliver! I'm definitely going to look into the FSA option and reach out to my wife's HR about getting that premium breakdown letter. One quick question - when you mention deducting qualified medical expenses as business expenses, do you have any examples of what kinds of things beyond ergonomic equipment might qualify? I work from home full-time and have been dealing with some back issues that I suspect are related to my home office setup. Would things like a standing desk or ergonomic chair potentially be deductible if they're medically necessary? Also, did you need any special documentation from a doctor to support those types of deductions, or was it sufficient to just have receipts showing the medical necessity?

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