Has anyone else noticed that their tax refund changes dramatically when entering the 1098-T information? When I first entered mine (also with $0 in box 1), my refund went DOWN by $2800! Then when I added my actual payment date and amount for spring semester, it went back UP by $3000. This is confusing as hell.

This entire thread has been incredibly helpful! I'm dealing with almost the exact same situation - Box 1 showing $0 but I definitely paid tuition in early 2023 for spring semester that was billed in December 2022. What's really frustrating is that my university's financial aid office gave me the runaround for weeks, telling me the form was "correct" because of their billing system. It's reassuring to see from @Noland Curtis that this is a known issue and that universities are supposed to be using the payment method, not the billing method. I'm going to follow the advice here and enter my actual January 2023 payment amount when FreeTaxUSA asks about expenses paid in 2023 but billed in another year. Like @Diez Ellis mentioned, my refund dropped significantly when I first entered the 1098-T, but I'm hoping it will bounce back once I add the correct payment information. Thanks everyone for sharing your experiences - it's made me feel much more confident about handling this correctly!

This thread has been incredibly helpful! My spouse and I are in the exact same boat - both over 55 with a family HDHP through my work. I was getting so frustrated with the conflicting advice from different sources. From reading everyone's experiences here, it sounds like the consensus is clear: we can indeed contribute the full $10,300 ($8,300 family limit + $1,000 catch-up for each spouse), but we absolutely need separate HSA accounts to do this correctly. I'm planning to keep things simple like several of you suggested - continue having the full family contribution come through my employer's payroll deduction, and then have my spouse open her own HSA account just for her $1,000 catch-up contribution. One follow-up question for the group: for those who went the route of opening that second HSA account primarily for the catch-up contribution, did you find any particular providers that were better for smaller account balances? I'm wondering if there are minimum balance requirements or fees that might make it less worthwhile for an account that might only see $1,000 per year initially. Thanks again everyone - this community is so much more helpful than my company's benefits hotline!

I just went through this exact situation and wanted to share what I learned from my tax preparer. You're absolutely right that you can contribute the full $10,300 total for 2025! Here's the breakdown that finally made it click for me: - The $8,300 family limit is like a "pool" that you can divide between your two HSA accounts however you want - Each $1,000 catch-up contribution must go into the specific person's HSA account (so yours goes to your account, your wife's goes to her account) - Total potential: $8,300 + $1,000 + $1,000 = $10,300 The key thing that confused me initially was thinking that having a "family" plan somehow limited us to one catch-up contribution. But the IRS is clear that catch-up contributions are tied to the individual person being 55+, not the type of health plan you have. Since you mentioned your wife already opened her own HSA account, you're all set! We decided to keep our setup simple: I get the full $8,300 family contribution through payroll deduction into my HSA, and my wife contributes her $1,000 catch-up directly to her account. Works perfectly and keeps the record-keeping straightforward. Your HR person probably wasn't sure because this is one of those HSA rules that even benefits professionals sometimes get wrong. But you're definitely entitled to both catch-up contributions!

Don't forget the statute of limitations on this! If your car was repossessed in 2021 but the lender is just now sending the 1099-C in 2025, something seems off. The IRS generally requires lenders to issue the 1099-C in the year the debt was actually canceled, not years later.

@Mae Bennett, I went through something very similar when my truck was repossessed in 2022. The timing confusion is totally normal - lenders often wait months or even years before officially "canceling" the remaining debt, especially if they're still trying to collect or if the debt gets sold to collection agencies. Here's what I'd recommend: First, call the original lender (not any collection agency) and ask specifically about the 1099-C status. Get the exact date they consider the debt "canceled" - this determines which tax year it applies to. If they canceled it in 2024, it affects your 2024 taxes. If it was 2023, you might need to amend that return. The good news is you have options even without the physical form. Keep that official notice you received as documentation. You can report the canceled debt amount on your tax return using the information from that notice. Just make sure to explore the insolvency exclusion others mentioned - if your total debts exceeded your assets when the debt was canceled, you might not owe any taxes on it at all. Don't stress too much about "getting in trouble" - the IRS deals with missing 1099-C situations all the time. As long as you report the income (or properly exclude it), you'll be fine.

This is exactly the kind of situation where having professional guidance really pays off. I went through a similar F1 to H1B transition and initially tried to figure it all out myself, but the dual-status filing requirements can get pretty complex. One thing I'd add to the great advice already given - make sure you understand the "first year choice" election. Since you're switching to H1B, you might be eligible to elect resident alien treatment for the entire year starting from your first day of H1B status, which could simplify your filing significantly. This election allows you to be treated as a resident for the entire year rather than filing as dual-status. However, this election isn't always beneficial - it depends on your specific income situation, potential treaty benefits during your F1 period, and whether you had any foreign income. You'd need to run the numbers both ways to see which approach gives you a better outcome. Also, keep in mind that if you make the first year choice, you'll be subject to tax on worldwide income for the entire year, not just US-source income during your F1 period. This could increase your tax liability if you had foreign income or investments. The substantial presence test calculation you mentioned is correct, and yes, you need to meet BOTH the 31-day and 183-day requirements to be considered a resident alien under that test.

I've been following this thread and wanted to add a few practical tips from my own F1-to-H1B experience that might help: 1. **Document everything**: Keep copies of your I-20, I-94 records, H1B approval notice, and paystubs from both periods. The IRS may ask for proof of your status change dates. 2. **FICA refund possibility**: While others mentioned you can't get FICA refunds for H1B period taxes, double-check if your employer incorrectly withheld FICA during any "cap-gap" period when you might have still been on F1 status. I recovered about $400 this way. 3. **State taxes**: Don't forget that state tax rules might be completely different from federal rules. Some states don't follow the substantial presence test at all and have their own residency criteria. 4. **Professional help**: Given all the complexity discussed here (dual-status filing, first year choice election, treaty considerations), it might be worth paying for a tax professional who specializes in nonresident/visa issues, especially for your first year with this situation. The cost often pays for itself through proper optimization and avoiding errors. The good news is that once you understand the process for your first dual-status year, future years become much more straightforward!

Just to add some more confusion lol - make sure you're also reporting any dividends properly if your ESPP shares paid any. Those would be on a separate 1099-DIV typically. Nothing is ever simple with stock compensation!

This thread has been incredibly helpful! I'm dealing with a similar ESPP situation but have an additional wrinkle - my company was acquired mid-year and I had shares from both the old company's ESPP and received cash-out payments for unvested portions. The acquiring company's HR said the cash-out should be on my W2, but I'm not seeing it clearly separated. Has anyone dealt with ESPP complications during M&A? I'm worried I'm missing something important for my tax filing.