Do you know if the IRS has any specific format requirements for digital copies? Like do they need to be PDFs or can they be any image format? My ADP downloads are PDFs but I've scanned some other documents as JPGs.

There's no specific format requirement from the IRS for personal recordkeeping. They just need to be legible and complete if you're ever asked to produce them. PDFs are generally better than JPGs because they maintain document formatting and are more printer-friendly, but either is acceptable. I'd recommend converting everything to PDF for consistency though. There are tons of free tools online that can convert image files to PDFs. Makes it easier to organize and find things later on. Also, make sure your scanned images capture ALL information from the document including the fine print - sometimes that becomes important during an audit.

Tax transcripts don't show everything. They show the summary info that was reported to the IRS but not all the supporting details. For example, you might see the total W-2 amount but not the breakdown of federal vs state withholding or retirement contributions. Also, getting transcripts can be a hassle sometimes with the IRS verification process.

I tried calling Computershare yesterday but got stuck in their automated system. What number did you use to reach an actual person? Did you have to provide any specific documentation to prove your non-US status?

For Computershare, try +1-781-575-2879 which is their dedicated international line. The trick is to press 0 twice after the initial greeting to bypass the menu system. For documentation, they asked me for a copy of my foreign passport and a utility bill or bank statement showing my foreign address. Having these ready when you call will speed things up. Also, ask specifically to speak with someone in their tax department since regular customer service folks sometimes don't understand the nuances of international tax forms. Be prepared to explain clearly that you're not a US person and need to replace a W-9 with a W-8BEN. In my experience, they'll email you a new form to complete within a day or two.

Yes! This happened to me. Had to file a 1040NR to reclaim the difference between what should have been withheld and what actually was. Such a pain.

Oh crap, I didn't even think about that. I've received about $630 in dividends this year already. Any idea how I would check if they withheld the right amount?

I hadn't even thought about checking if the amounts are correct! Where exactly would I find Box 1 and Box 5 on the form? And if something isn't right, do I just call the financial aid office?

Box 1 is near the top of the form labeled "Payments received for qualified tuition and related expenses" and Box 5 is labeled "Scholarships or grants." Compare those amounts to your actual payment records and financial aid statements. If you notice a discrepancy, yes, call your school's financial aid office or sometimes they have a dedicated bursar or student accounts office. Explain the issue and ask them to issue a corrected 1098-T. They're usually pretty good about fixing these errors since they're required by law to report accurate information to the IRS.

This is good advice! I lost access to my 1098-Ts after graduating and had to pay my old university $25 per form to get copies when I needed them later. Such a pain.

That distinction makes a lot of sense, thank you! In my case, I paid for a specific procedure that was scheduled for the following year, so it sounds like I can deduct it on my 2022 taxes. And yes, even with this expense added, my medical costs will be about 9.2% of my AGI for 2022, so I should benefit from the deduction. I'm definitely itemizing because my mortgage interest and state taxes already put me well over the standard deduction amount.

Do credit card statements count as proof of payment date? I have a lot of medical expenses but didn't keep all the paper receipts.

Does H&R Block have a free version? Cash App and FreeTaxUSA are appealing because they offer free or really cheap filing options. I don't want to spend $50+ on tax prep if I can avoid it.

H&R Block does have a free version but like all the "free" tax services, it's only free for simple returns. If you have anything slightly complicated (investment income, self-employment, itemized deductions, etc.), you'll end up having to upgrade to a paid version. Honestly, FreeTaxUSA is probably your best bet for affordable filing - their federal filing is free and state is only like $15. Cash App might be convenient for banking, but as you've discovered, it's pretty limited as a tax service. Whatever you choose, just stick with ONE service next year to avoid this headache!

Nothing complicated really - just standard W-2 income from one job and some basic interest income from my savings account. No major life changes or anything fancy. I just got lured in by Cash App's free filing and didn't realize they couldn't do my state taxes until after I'd already submitted the federal return.

If it's a simple return like OP described, they should definitely be able to file state-only through most services. I've used TurboTax for state-only before when I had a similar situation. Just make sure to select "I've already filed my federal return" option when you start.