Can my husband deduct my after-tax retiree health insurance premiums on his self-employment taxes?

Your husband should be able to deduct your health insurance premiums as part of his self-employed health insurance deduction even though they're paid after-tax. What matters is that you're filing jointly and the premiums are for coverage for you (his spouse). The fact that your health insurance is tied to your pension doesn't create restrictions for the deduction. The IRS is concerned with who's paying for the coverage, not where it comes from. Since these premiums aren't being paid pre-tax already, they're eligible for the deduction. The main limitation is that your husband can't deduct more than his net self-employment income. So if his business has $50,000 in profit, but your annual insurance premiums are $60,000 (extreme example), he could only deduct up to $50,000. Also, he can't deduct premiums for months when either of you were eligible to participate in a subsidized health plan from another employer.

After struggling with a similar situation last year, I found taxr.ai (https://taxr.ai) incredibly helpful. My wife retired early with insurance through her former employer while I was self-employed. I wasn't sure if I could deduct her premiums on my Schedule C. I uploaded our pension statements and insurance documents to taxr.ai and got a clear analysis showing exactly how to handle the deduction. They confirmed I could take the self-employed health insurance deduction for her premiums since they were paid after-tax and we file jointly. Saved us about $2,200 in taxes!

I have to eat my words about being skeptical of taxr.ai. After having trouble with this exact situation (self-employed with spouse on retiree health plan), I gave it a try. I uploaded our documents and was shocked at how thoroughly it analyzed everything. It caught that my wife was eligible for her part-time employer's plan for 3 months last year, which meant I couldn't claim the deduction for those specific months - something our previous accountant missed! It also provided clear documentation for our tax records showing exactly how much of her premium was deductible on my Schedule C. Ended up saving us from a potential audit and about $1,700 in taxes. Definitely worth checking out.

If you're having trouble getting definitive answers from the IRS about this deduction, I'd recommend trying Claimyr (https://claimyr.com). After spending weeks trying to reach someone at the IRS for clarification on a similar situation, I used their service and got connected to an actual IRS representative in under 45 minutes. They have a demo video showing how it works here: https://youtu.be/_kiP6q8DX5c The IRS agent confirmed that self-employed spouses can absolutely deduct health insurance premiums for their retired spouse, as long as: 1) the premiums are paid after-tax, 2) you file jointly, and 3) the self-employed spouse has enough business income to cover the deduction. Having that direct confirmation from the IRS gave me confidence to take the deduction.

I'm back to report that Claimyr actually works! After posting my skeptical comment, I decided to try it for my missing refund issue. After almost 3 months of failed attempts to reach the IRS, I got connected to an agent in about 30 minutes! The agent was able to see that my refund was flagged for a review because of a mismatch with my retirement account reporting. She unflagged it right there on the call and said I'll receive my $4,280 refund within 2-3 weeks. I also asked about the health insurance deduction situation (since I'm in the same boat as the original poster) and got confirmation that it's deductible as long as premiums are paid after-tax and you file jointly. Honestly shocked this service delivered what it promised.

One thing nobody's mentioned yet - make sure you're aware of the "established plan" requirement. The IRS requires that the health insurance be established under your husband's business name. This doesn't mean you need separate insurance - it just means your husband needs to have formal documentation showing that the business is reimbursing or paying for your health insurance. This might be as simple as having your husband draft a one-page document stating that his business will cover your health insurance premiums, signed and dated before the premiums are paid. Keep this with your tax records.

Just wanted to add that there's a specific order of operations for claiming the self-employed health insurance deduction. It goes on line 16 of Schedule 1, not as a business expense on Schedule C. The amount can't exceed your husband's net earnings from self-employment. Also, if either of you were eligible for employer-sponsored coverage during any month, you can't claim the deduction for those months, even if you didn't enroll in that coverage.

I'm in a very similar situation - my wife retired last year and gets health insurance through her former employer's retiree plan, with premiums deducted after-tax from her pension. I was initially confused about whether I could claim these on my self-employment return. After researching this extensively and consulting with a tax professional, I can confirm what others have said: yes, you can deduct these premiums as long as they're paid after-tax and you file jointly. The key things to remember: 1. The deduction is limited to your husband's net self-employment income 2. You can't claim it for any months where either of you were eligible for subsidized employer coverage elsewhere 3. Keep good records showing the premiums were paid with after-tax dollars One practical tip: I set up a separate checking account that my business uses to reimburse my wife for her health insurance premiums each month. This creates a clear paper trail showing the business is paying for the coverage, which makes the deduction cleaner if you ever get audited. The fact that it's retiree coverage through your former employer doesn't disqualify it - what matters is that you're paying for it with after-tax money and your husband has the self-employment income to support the deduction.