Just wanted to add - make sure you keep copies of EVERYTHING related to your nondeductible contributions forever (or at least until you've withdrawn all the money). I learned this the hard way. I had made nondeductible contributions years ago, filed my 8606 forms properly, but then lost track of the paperwork during a move. When I started taking distributions years later, I couldn't prove my basis to the IRS and ended up paying tax on money that should have been tax-free coming out. The burden of proof is 100% on you to track your nondeductible basis, not on the IRS. They don't keep easily accessible records of your basis year to year.

Great advice from everyone here! I went through this exact situation last year when I discovered I had missed filing Form 8606 for multiple years of nondeductible contributions. One thing I'd add that helped me tremendously - when you mail your Form 8606, use certified mail with return receipt requested. The IRS can be slow to process these forms, and having proof of delivery gives you documentation that you filed it timely (even though it's late for the original tax year). Also, consider keeping a detailed log of all your IRA transactions going forward. I created a simple spreadsheet that tracks: - Date of contribution - Amount contributed - Tax year it applies to - Whether it was deductible or nondeductible - Form 8606 filing status This has made my annual tax prep so much easier and ensures I never miss tracking my basis again. The few hours spent organizing this information upfront saves tons of stress later, especially if you ever need to prove your basis to the IRS during an audit or when taking distributions. Your numbers look correct for the 2022 form, and yes, you should include the full $15,500 basis on your 2023 Form 8606 even if the 2022 form hasn't been processed yet. The key is that you're filing it before or with your 2023 return.

As someone who's been through the audit process, I want to emphasize what Natasha said about documentation. Even if you had a qualifying medical expense, the IRS will want extensive documentation during an audit - not just a doctor's note, but detailed records showing the medical necessity, treatment plan, and how the expense specifically addresses your diagnosed condition. For your Planet Fitness situation, even if you kept perfect records, the fundamental issue is that general gym memberships don't qualify regardless of medical recommendation. The IRS has consistently ruled that these are personal expenses for general health maintenance. One thing I learned the hard way: it's better to miss a legitimate deduction than to claim a questionable one. The stress and cost of dealing with an audit far outweigh the tax savings from a gym membership deduction. Focus on the clear-cut deductions for your freelance business instead - those are much more valuable and defensible.

This thread has been incredibly helpful! As someone who's also self-employed and was wondering about similar deductions, I really appreciate all the detailed explanations from the tax professionals here. I've been making the same mistake of thinking that anything health-related recommended by a doctor might be deductible. The distinction between "general health maintenance" vs "treatment of a specific condition with qualified medical personnel" that Natasha explained really cleared things up for me. It's also eye-opening to learn about the 7.5% AGI threshold - I had no idea medical deductions had such a high bar to clear before they even start helping. Between that and the standard deduction being so high, it sounds like most of us probably won't benefit from medical expense deductions anyway. Thanks everyone for sharing your experiences and expertise. This community is so much more helpful than trying to wade through confusing IRS publications on my own!

Just to add to what others have said - make sure you're keeping DETAILED records. I got audited on this exact issue with my consulting business. What saved me was having: 1) Course descriptions printed from the university website 2) A statement I wrote explaining how each course applied to my current business 3) Client invoices showing I was doing related work before starting the degree 4) The letter from the company saying this education was necessary The IRS agent told me most people fail these audits because they can't show the direct connection between the education and existing business. Don't just say "MBA helps my business" - be super specific about how accounting class X improves service Y that you were already providing.

This is a great question that many contractors struggle with! Based on my experience helping clients with similar situations, you're on the right track with the business expense deduction approach. Since your wife receives 1099-NEC income, she's considered self-employed, which actually gives you more flexibility than W2 employees have. The key is demonstrating that the MBA maintains or improves skills she's already using in her existing business activities. From what you've described, her current work already involves finance, accounting, operations, and HR - and the MBA coursework directly relates to these areas. This creates a strong case for the "maintains or improves existing skills" test. A few important points to consider: 1) Deduct these on Schedule C as ordinary business expenses, not as itemized deductions 2) The letter from the company will be helpful supporting documentation 3) Keep detailed course syllabi showing how each class relates to her current work 4) Document her existing business activities before starting the MBA One thing to be cautious about - make sure the MBA isn't positioning her for a completely different profession. Since she's already working in business consulting and the coursework enhances those existing skills, you should be fine. The business expense deduction will likely be more beneficial than education credits at your income level, as it reduces both income tax and self-employment tax on her Schedule C income.

As someone who's dealt with this exact situation before, I'd recommend trying the IRS's own Form 1040 online if you have a relatively straightforward return. While it's not as polished as commercial software, it does allow you to input your already-calculated numbers directly without having to redo all your work from scratch. The key advantage is that since you've already done all the math and have your PDFs as reference, you're essentially just transcribing the final numbers into their system. It's tedious but much faster than starting over with a full-service tax program. One tip: keep your PDFs open in separate browser tabs so you can easily copy the numbers over. The IRS system will validate your entries and catch any obvious errors, which gives you some peace of mind that everything transferred correctly. If your return is more complex (multiple schedules, business income, etc.), then the AI-powered solutions mentioned above might be worth the cost to avoid manual data entry.

I'm in a similar boat this year! I've been using FreeTaxUSA to create my forms but ran into the same roadblock when trying to eFile. After reading through all these suggestions, I think I'm going to try the taxr.ai route that @Luca Marino recommended. The idea of not having to re-enter all my data is really appealing, especially since I spent so much time getting everything perfect in my PDFs. One question though - for those who have used these AI-powered tax services, do they handle amended returns if something gets messed up during the conversion process? That's my biggest concern about letting software interpret my documents rather than doing direct data entry myself. @Sean Murphy - let us know which option you end up going with! I'd be curious to hear how it works out since we're in basically the same situation.

I went through something very similar last year with my EITC return! Three months is definitely frustrating, but unfortunately not unheard of for EITC claims. A few things that might help: First, definitely check your mail thoroughly - the IRS often sends verification letters for EITC returns that can look like junk mail. If you missed one of these, it could explain the entire delay. Second, try checking your transcript on the IRS website rather than just the Where's My Refund tool. The transcript will show actual processing codes that can tell you exactly what's happening. Look for codes like 570 (additional review) or 971 (notice issued). Also, don't panic about the "received" vs "accepted" status - the Where's My Refund tool is notoriously unreliable with its terminology. Your return was likely accepted if you got that initial confirmation from FreeTaxUSA. One last tip: if you do need to call the IRS, try calling right when they open (7 AM local time) on Tuesday or Wednesday. Still difficult to get through, but slightly better odds. Hang in there - EITC returns just take longer, but you should get your refund eventually!

I'm dealing with almost the exact same issue! Filed in late January with EITC and my refund has been stuck on "received" for over 2 months now. Reading through these responses has been incredibly helpful - I had no idea about checking the transcript or that EITC returns routinely take 45-60 days even without issues. I'm definitely going to try creating an IRS account to check my transcript first, since that seems like the most reliable way to see what's actually happening. The processing codes sound way more informative than the vague "received" status I've been staring at for weeks. Also going to double-check my mail pile for any IRS letters - the comment about verification letters looking like junk mail really caught my attention. I've been so focused on the online tools that I might have overlooked something important in the mail. Thanks everyone for sharing your experiences and solutions. It's reassuring to know this level of delay isn't necessarily a sign that something went wrong with my return!