No kids unfortunately. It was just me and my ex-wife. We don't have any dependents together, and no one else lived with us. Based on what everyone's saying, looks like I'm stuck with the Single filing status and this huge tax bill. Just wish I'd known about this earlier in the year so I could have adjusted my withholdings.

That's tough, sorry to hear it. Without a qualifying dependent, you're right that Single is your only option. For next year, definitely update your W-4 with your employer ASAP to avoid withholding problems. One thing to consider is whether you might qualify for any tax credits based on your situation. The Saver's Credit could apply if you contributed to retirement accounts and your income isn't too high. There might also be education credits if you paid any tuition or student loan interest.

This is good advice. Also, don't forget about any legal fees specifically related to tax advice during your divorce. Those might be deductible too, even though general divorce attorney fees aren't. My accountant helped me identify about $1,800 in deductible legal fees from my divorce last year that were specifically for tax consultation.

Yes, most required fees DO count as qualified expenses! If the fees are required for enrollment or attendance, they count. The only fees that don't count are those for room and board, transportation, or personal expenses. So your technology fee and similar required fees would be included in your qualified expenses total.

That's really helpful, thank you! So it sounds like both my tech fee and health services fee would count since they're mandatory for enrollment, but something like a parking pass wouldn't count since that's transportation-related. My school also offers an optional sports package - since that's not required, I assume that doesn't count as a qualified expense either?

Not a stupid question! Most schools don't mail them anymore. Check your student account/portal for a section called "Tax Forms" or sometimes "1098-T Electronic Consent." Schools were required to make them available by January 31st. If you can't find it online, contact your school's bursar or student accounts office - they're the ones who generate these forms. Sometimes they're in weird places like the financial aid section rather than where you'd expect.

That's really helpful to know! I'll definitely be paying my accountant to help sort this out. Do you know if there's a specific way I should document these fees to make it clear they're related to my business rather than personal tax preparation?

Ask your accountant to itemize their invoice to clearly show the time spent dealing with the business retirement plan issues. The description should specifically mention "consulting services for business retirement plan compliance" or similar business-focused language. Keep this invoice with your business records, not just your tax records. If the accountant's work includes both personal and business tax matters, having them provide separate invoices for the business portion is even better. Clear documentation of the business purpose is your best protection in case of questions later.

I went through this last year. For excess employer contributions in a solo 401k, your plan administrator will issue a 1099-R with code "E" if you do a corrective distribution. You'll owe income tax on any earnings from the excess amount, but it's better than paying the excise tax year after year. However, if you're the administrator of your own solo 401k (many self-employed people are), you'll need to generate the 1099-R yourself, which can be tricky. I ended up hiring someone just for that part.

We have an HDHP with an HSA that we max out, but I'm confused about how the employer stipend affects the Premium Tax Credit. Our plan isn't through the marketplace - does that automatically disqualify us?

Yes, that's a key point I should have clarified - to qualify for the Premium Tax Credit, you must purchase your health insurance through the Health Insurance Marketplace (Healthcare.gov or your state's exchange). If you bought your insurance privately outside the marketplace, you won't be eligible for the Premium Tax Credit regardless of your income. For your HSA, you're making a smart move by maxing it out! The stipend doesn't affect your HSA contribution limits at all. You'll still get the full tax deduction for your HSA contributions even while receiving the stipend, which is one of the few "double benefits" allowed in the tax code.

I used TurboTax last year with a similar situation. It did ask about health insurance and whether I received any stipends, but I found it confusing. I had to manually make sure the stipend was included as income (mine was on my W-2 already). The medical expense deduction part worked fine though - it walked through itemizing and the 7.5% AGI threshold clearly.

I tried freetaxusa instead of TT and it handled my health insurance stipend situation perfectly. It specifically asked if I received any benefits for health insurance and guided me through reporting it correctly. Much cheaper than TT too!

Thank you so much for mentioning the CP01A notices! I just realized I probably did receive that letter back in Dec 2021 for my 2022 PIN but didn't realize I needed to keep it. Is there any way to request a copy of an old CP01A notice, or do I still need to go through the retrieval process?

You can request a transcript of your account from the IRS which might show the CP01A was issued, but it won't contain the actual PIN number. Unfortunately, the IRS doesn't typically resend copies of old CP01A notices with the exact PIN. Your best bet is to use the online IP PIN retrieval tool as others have mentioned, or contact the IRS directly. Since you've already successfully recovered your 2023 PIN online, try that same process to see if your 2022 PIN is visible there as well. If not, you'll likely need to call the dedicated Identity Theft line at 800-908-4490 where they can verify your identity and provide any prior year PINs that were issued to you.

That approach might cause problems. If the IRS has already assigned you an IP PIN, you MUST use it when filing. Filing Form 14039 is for reporting identity theft initially, not for bypassing an already established IP PIN requirement. Paper filing without your PIN will likely result in processing delays and possible rejection.