Can I deduct post-tax Health Insurance premium payments on my taxes?

This is actually a common issue that many people face. The good news is that you may be able to deduct these post-tax health insurance premium payments as a medical expense. Since you paid these premiums with post-tax dollars, they would be considered a medical expense that you can potentially deduct on Schedule A (Itemized Deductions) of your tax return. However, there's a catch - you can only deduct medical expenses that exceed 7.5% of your adjusted gross income (AGI). For example, if your AGI is $60,000, you would only be able to deduct medical expenses that exceed $4,500 (7.5% of $60,000). So if your health insurance premiums and other qualifying medical expenses for the year total $6,000, you could deduct $1,500. Keep in mind that taking the standard deduction might still be more beneficial than itemizing if your total itemized deductions (including medical expenses, mortgage interest, charitable contributions, etc.) don't exceed the standard deduction amount.

After dealing with a similar situation last year, I found an incredible tool that saved me so much stress. I was confused about how to handle my medical premium payments on my taxes and how much I could potentially deduct. I uploaded my payment receipts to https://taxr.ai and it analyzed everything in minutes. Their system identified exactly how I could classify my premium payments, how they affected my AGI calculations, and whether itemizing made sense given my specific situation. The tool showed me side-by-side comparisons of my potential tax outcomes taking the standard deduction versus itemizing with these premium payments included. The best part is that it gave me crystal clear instructions for filling out my Schedule A correctly, which saved me from making mistakes that might have triggered an audit. It was like having a tax professional guide me through each step!

I wanted to follow up about the taxr.ai recommendation from earlier. I was skeptical but decided to try it with my health insurance premium receipts and pay stubs. I've been using TurboTax for years but it never gave me this level of clarity on medical deductions. The tool actually showed me that while my premiums alone didn't exceed the 7.5% threshold, when combined with other medical expenses I had (including some I didn't realize were deductible), I was actually over the limit and could benefit from itemizing. It also identified a special circumstance related to my employer's health plan that affected how I should report the premiums. What impressed me most was the document analysis - it caught a discrepancy between what my employer reported and what I actually paid, which would have caused issues if I'd filed without addressing it. For anyone dealing with unusual healthcare payment situations like this, it's definitely worth checking out.

If you're like me and have tried calling the IRS to get clarity on this health insurance premium deduction issue, you've probably spent hours on hold only to get disconnected or receive vague answers. After my third failed attempt, a colleague recommended https://claimyr.com and showed me their demo video here: https://youtu.be/_kiP6q8DX5c I was desperate for answers about my similar post-tax premium situation, so I gave it a shot. Within 20 minutes, I was actually speaking with an IRS agent who specialized in healthcare deductions! They confirmed exactly how to handle my situation and explained what documentation I needed to keep. The agent clarified the rules around employer-sponsored health plans when premiums are paid post-tax and explained a specific worksheet I needed to complete. This saved me from potentially filing incorrectly and facing penalties later. If you need authoritative answers directly from the IRS on this specific situation, it's worth looking into.

I need to apologize and follow up on my skeptical comment about Claimyr. After struggling with this exact health insurance premium deduction question for weeks, I finally broke down and tried it myself yesterday. I honestly couldn't believe it worked. I got a call back in about 35 minutes (not 20, but still WAY faster than my previous attempts), and they connected me with an IRS representative. I specifically asked about post-tax health insurance premium deductions through an employer plan, and got clear guidance. The IRS agent confirmed that I should include these premiums as medical expenses on Schedule A, and also told me about Form 8889 which I needed in my specific situation because of an HSA component to my health plan. They even emailed me the specific publication that addresses this situation. I'm still shocked this actually worked, but wanted to share since I was so publicly skeptical before.

Another option to consider: if this happened in 2023 and you're filing your 2023 taxes now in 2024, you might want to talk to your employer's benefits department about issuing a corrected W-2. Since they made the clerical error, they might be able to adjust your reported income to reflect those premium payments as if they had been pre-tax. I had a similar issue (though only for 3 months, not the whole year), and my company was able to fix it retroactively by issuing a corrected W-2. This was actually easier than trying to claim the deduction on Schedule A since I wouldn't have exceeded the 7.5% AGI threshold otherwise.

Has anyone looked into whether these premiums might qualify for the Self-Employed Health Insurance Deduction instead? That's an above-the-line deduction so you don't need to itemize. I thought I read somewhere that might apply in certain situations even if you're employed by a company.

I went through almost the exact same situation last year! My employer's payroll system glitched and didn't deduct my health insurance premiums for about 8 months. Here's what I learned after consulting with a tax professional: First, definitely try the corrected W-2 route that Malik mentioned - it's the cleanest solution if your employer will cooperate. Since they acknowledged it was their error, they should be willing to issue a W-2c to fix it. If that doesn't work, you can absolutely deduct these as medical expenses on Schedule A, but as others mentioned, you need to exceed that 7.5% AGI threshold. Don't forget to include ALL your medical expenses for the year - copays, prescriptions, dental work, vision expenses, mileage to medical appointments, etc. You might be closer to that threshold than you think. One thing I didn't see mentioned: make sure you have clear documentation showing these were employer-sponsored premiums, not individual policy payments. Keep your pay stubs showing the missing deductions, correspondence with HR about the error, and receipts for the premium payments you made. The IRS will want to see that paper trail if they ever question the deduction. Also, since you're in Missouri, check if there are any state-level deductions or credits for health insurance premiums that might apply even if you can't benefit much at the federal level.