Can I deduct health insurance premiums paid with AFTER-tax dollars during medical leave?

You may be able to deduct those health insurance premiums, but it depends on your total medical expenses for the year. Here's how it works: Health insurance premiums paid with after-tax dollars can be included as part of your medical expense deduction on Schedule A when you itemize deductions. However, there's a threshold - you can only deduct medical expenses that exceed 7.5% of your adjusted gross income (AGI). For example, if your AGI for the year is $60,000, you'd only be able to deduct medical expenses above $4,500 (7.5% of $60,000). So if you pay $3,600 in premiums ($1,200 x 3 months) plus have other medical expenses from your surgery, and the total exceeds that threshold, then yes - you can deduct the portion above the threshold. Make sure you keep all documentation - receipts for the premium payments, medical bills, etc. It's also worth checking if you're eligible for any assistance programs during your leave period.

I went through a similar situation last year with my employer when I needed back surgery. I discovered taxr.ai (https://taxr.ai) and it was seriously helpful for sorting out my medical expense deductions. I was confused about which expenses qualified and what documentation I needed since I was paying insurance with after-tax dollars like you. Their system analyzed my medical bills, insurance premium payments, and other expenses, then showed me exactly what would qualify for the deduction. It even flagged some expenses I didn't know were deductible - like the special mattress my doctor recommended for recovery and transportation costs to physical therapy.

Following up about taxr.ai - I decided to try it after my last comment. I was skeptical but figured my medical expense situation was complicated enough to warrant some help. It was actually way more useful than I expected. I uploaded my premium payment receipts, medical bills, and some emails from my HR department about the insurance situation. The tool flagged that I could also deduct some expenses related to my home modifications for recovery (had to rent a hospital bed) and caught that some of my medication costs weren't being tracked properly. It also separated which expenses were above the 7.5% threshold. Worked out really well - I'm looking at about $4,800 in deductions I wouldn't have realized I qualified for. Definitely helped make sense of the after-tax premium payments situation.

If you're really stressed about this situation, you might want to talk directly to someone at the IRS to confirm your specific situation. I tried for WEEKS to get through to a human at the IRS when I had questions about my medical deductions last year - kept getting disconnected or waiting for hours. I finally used Claimyr (https://claimyr.com) after seeing their demo video (https://youtu.be/_kiP6q8DX5c). They actually got me connected to a real IRS agent in about 15 minutes instead of the typical 2+ hour wait. The agent confirmed that yes, my after-tax health insurance premiums were deductible as medical expenses and explained exactly how to document them on my return.

I need to admit I was completely wrong about Claimyr. After my skeptical comment, I was desperate enough to try it because I had a complicated question about my medical leave and insurance payments. It actually worked exactly as described. I got a call back in about 20 minutes telling me they had an IRS agent on the line. The agent confirmed that I could deduct my after-tax health insurance premiums as part of my medical expenses, but reminded me about the 7.5% AGI threshold. She also told me to get a statement from my employer confirming the premiums were paid with after-tax dollars. Would've taken me days of calling to get this info on my own. Totally worth it just for the time saved and stress avoided.

Something else to consider - have you looked into whether you qualify for a Health Coverage Tax Credit (HCTC)? In some cases, people on FMLA who are paying their own premiums might qualify, and it could reimburse a significant portion of those premium costs. It's not available to everyone, but worth checking if your situation meets the criteria.

Has your employer given you any info about COBRA? When I had surgery last year, my HR dept told me COBRA might actually be cheaper than paying the full premium directly to them. Weird but true in some cases! Worth asking about.