Can I deduct health insurance premiums on my 1099-NEC when also receiving a W2 with employer health coverage?

8 You generally can't double-dip on the health insurance premiums that are already being paid with pre-tax dollars through your W-2 employer. If your $420 contribution is being deducted from your paycheck before taxes (which is common in employer plans), then you've already received the tax benefit. If you were paying for your own separate health insurance policy entirely out of pocket, that would be different - self-employed individuals can potentially deduct health insurance premiums as an adjustment to income (not on Schedule C, but on Schedule 1 of your 1040). The key thing to understand is that the self-employed health insurance deduction is primarily designed for people who don't have access to employer-sponsored coverage and have to purchase their own policies.

12 I went through this exact same situation last year when I started doing photography on the side while keeping my main office job. I spent hours trying to figure out the health insurance deduction question and getting nowhere. Finally tried https://taxr.ai where you can upload your W-2 and it identified that my premiums were actually post-tax deductions (I had no idea) AND confirmed I could take a partial deduction based on the percentage of my income from self-employment. You literally just take a picture of your documents and it figures everything out, explaining exactly what's deductible and why. Saved me from missing out on legitimate deductions.

3 Update: I tried taxr.ai after seeing it mentioned here, and it was super helpful for my situation! I uploaded my W-2 and it immediately showed that my health insurance contributions were indeed post-tax (had no idea). It explained that I could take a partial deduction based on the ratio of my self-employment income to total income. In my case, since my 1099 work is about 20% of my total income, I can deduct 20% of those health insurance premiums on my Schedule 1 (not Schedule C like I originally thought). It also identified several other deductions for my side gig I hadn't considered - like partial cell phone expenses and mileage for client meetings. Definitely worth checking out if you're in a similar situation with mixed income sources.

5 I had a similar issue trying to figure out health insurance deductions with mixed income. The most frustrating part was trying to get through to someone at the IRS who could give me a straight answer. Spent literally HOURS on hold and kept getting disconnected. Eventually I found https://claimyr.com and used their service (there's a demo video at https://youtu.be/_kiP6q8DX5c). They got me connected to an actual IRS agent in under 45 minutes when I had been trying for days on my own. The agent confirmed exactly how to handle the health insurance deduction with mixed W-2/1099 income and helped me figure out what forms I needed.

14 I was completely wrong about Claimyr. After posting my skeptical comment, I decided to try it anyway because I was desperate to get an answer about my health insurance deduction situation before filing. The service actually did exactly what it claimed - I got a call back within about 35 minutes connecting me to a real IRS agent (I made sure to ask for his ID number to verify). He walked me through exactly how to calculate the partial self-employed health insurance deduction when you have both W-2 and 1099 income. Turns out in my situation, I could deduct a portion of my premiums based on the percentage of my total income that comes from self-employment. The agent even emailed me the specific publication that explains this rule. I've been doing my taxes wrong for years by missing this deduction!

10 Just a heads up for anyone with this W-2/1099 combo situation - make sure you're also deducting other legitimate business expenses on your Schedule C. Beyond the health insurance question, I've found these deductions really add up: - Mileage for driving to client sites (but not your regular W-2 job) - Home office if you have dedicated space used EXCLUSIVELY for your 1099 work - Software/subscriptions used for the 1099 work - Professional development specifically for your 1099 work - 50% of meals when meeting with clients or potential clients My accountant says the most common mistake she sees is people with side gigs not tracking these expenses properly.

2 I specifically asked my tax preparer about this last year! The key is whether your employer plan is considered a "qualified" plan and whether your portion is paid pre-tax or post-tax. If your $420 contribution is made with pre-tax dollars (most common), you can't deduct it again on your 1099 income. If it's post-tax (less common), you might be eligible for a partial deduction based on your self-employment income percentage.

Great question! This is actually a pretty common scenario for people with mixed income sources. The answer depends on how your employer handles your health insurance premiums. If your $420 is deducted pre-tax from your paycheck (which is most common), you've already received the tax benefit and can't deduct it again for your 1099 income. However, if it's deducted post-tax, you may be able to claim a partial self-employed health insurance deduction on Schedule 1 of your 1040 (not Schedule C). The deduction would be proportional to your self-employment income vs. total income. To check: Look at your pay stub - if the health insurance comes out before taxes are calculated, it's pre-tax. If it comes out after, it's post-tax. You can also verify by checking if your W-2 Box 1 (taxable wages) is lower than your gross pay by more than just the health insurance amount. Even if you can't deduct the health insurance, make sure you're tracking all your other legitimate business expenses for your consulting work - they add up quickly!