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.

As someone who's been doing freelance digital art for about 3 years now, I can definitely relate to the tax confusion when starting out! You're asking all the right questions. One thing I wish I'd known earlier - keep track of your business expenses from day one, even small ones. I missed out on deducting things like PayPal fees, bank transfer fees, and even the cost of business cards or promotional materials in my first year because I didn't realize they counted. Also, since you mentioned you're keeping good records with spreadsheets, make sure you're also tracking your expenses in the same detail. I use separate columns for income source, expense category, and business percentage (like if I use my phone 30% for business vs personal). This makes Schedule C so much easier to fill out. For the quarterly payments, don't stress too much about the ones you've missed - the penalties are usually pretty small for first-time filers, especially if you're not making huge amounts yet. Just try to get current with the next payment and you'll be fine. The IRS also has a really helpful Publication 334 (Tax Guide for Small Business) that covers a lot of the self-employment basics if you want to read up on the details yourself.

One thing that really helped me when I started freelancing as a digital artist was setting up a separate business bank account, even though it's not required for sole proprietors. It makes tracking income and expenses so much cleaner, especially when tax time comes around. Since you mentioned you're making decent money ($4,200 in 6 months), you're definitely going to want to stay on top of those quarterly payments going forward. I'd suggest calculating what you think you'll make for the full year and then divide that by 4 for your remaining quarterly payments. Better to overpay slightly than get hit with penalties. Also, don't forget about state taxes if your state has income tax. Even though you mentioned your state doesn't charge sales tax on digital products, you'll still likely need to report your freelance income on your state return too. Each state handles this differently, so it's worth looking into your specific state's requirements for self-employment income. The good news is that once you get through your first year and understand the process, it becomes much more routine. You're already ahead of the game by keeping good records and asking these questions early!

Has anyone tried requesting a penalty abatement for first-time late filing? I heard the IRS has a First Time Penalty Abatement policy where they'll waive penalties for people with clean previous filing history.

I'm going through something similar with my divorce proceedings - needed my 2021 return for financial disclosure and realized I never actually submitted it either! The stress is real when you need these documents for court. A few things that helped me: First, definitely file 2022 immediately as a separate return. The IRS systems are set up to handle each tax year individually, so there's no option to combine years anyway. For the court documentation, consider asking your attorney if they'll accept a copy of your prepared return along with proof that you've submitted it to the IRS (like a certified mail receipt if you file by paper, or the electronic confirmation if you e-file). Courts understand that IRS processing can take weeks, so they often accept evidence that you've filed rather than waiting for the processed return. Also, once you do file, you can request an Account Transcript from the IRS online at irs.gov which will show your filing status and any penalties/payments. This can serve as official documentation for court purposes while you wait for your actual return to be processed. The penalties will hurt, but getting this resolved quickly is more important than the extra money, especially with court deadlines looming. Good luck!

Has anyone used the "last-month rule" instead of prorating in situations like this? From what I understand, if you're eligible on December 1st, you can contribute the full annual amount (individual or family based on December status) as long as you remain eligible through the end of the following year. Would that work in the original poster's situation?

This is a great breakdown of how to handle HSA contributions with mid-year coverage changes! I wanted to add one important point about timing that might help others in similar situations. When making these prorated contributions, you have until the tax filing deadline (typically April 15th of the following year) to make HSA contributions for the previous tax year. So even though you're figuring this out now, you still have time to make the calculated $6,450 contribution for 2023 if you haven't already maxed it out. Also, make sure to keep detailed records of the coverage change dates and your calculations. The IRS may want documentation if they ever question your contribution amounts, especially with the complexity of mid-year switches between family and individual coverage. Your insurance company should be able to provide letters or statements showing exactly when coverage types changed. Congratulations on the pregnancy, by the way! Once your little one arrives, you'll likely be able to switch back to family HDHP coverage and family contribution limits if that makes sense for your situation.

Has anyone tried using one of those Certified Acceptance Agents instead of going directly through the IRS? The thought of sending my wife's original passport in the mail is making me really nervous...

Just to add some clarity for anyone else in this situation - you absolutely can apply for an ITIN after filing your return! I went through this exact process with my partner last year. The key things to remember: 1. Use Form W-7 and include a complete copy of your already-filed tax return as supporting documentation 2. If you're nervous about mailing original documents (totally understandable!), definitely look into using a Certified Acceptance Agent - they can verify originals in person and submit copies 3. The ITIN application won't affect your already-filed return for this year, but it will give you more filing options next year The whole process took about 10 weeks for us when we went through a CAA. Yes, there's a small fee, but the peace of mind was worth it. Don't stress too much - this is a pretty common situation and the IRS handles it regularly!