I've used both TurboTax and FreeTaxUSA in the past couple years. TurboTax actually does have a dedicated section for Box C transactions, but it's buried deep in their investing section and not intuitive to find. FreeTaxUSA is more straightforward overall and way cheaper, but like OP mentioned, it has this quirk with Box C. TaxAct was the worst of the ones I tried - it kept giving me errors with certain crypto transactions. H&R Block's software seemed decent for complex investment situations but costs more than FreeTaxUSA.

I've been looking into this more since posting. Apparently TaxHawk (which is basically the same engine as FreeTaxUSA) has the same limitation. TurboTax does technically support Box C transactions but I heard it's not easy to find. I'm sticking with FreeTaxUSA this year since I already entered everything, but might try TurboTax next year if I have more complex investments. The price difference is significant though - like $100+ more for TurboTax with investment support vs FreeTaxUSA.

That's super helpful! I didn't even think to check the final form. I just did that and you're right - even though I entered my Box C transaction in the Box B input section, on the actual 8949 PDF it shows up correctly under Box C. FreeTaxUSA must have some logic built in that recognizes certain types of transactions and moves them to the right category for the final form. That makes me feel a lot better about continuing to use them. Thanks for the tip!

Does this apply to social media influencers? My cat has an Instagram with 10k followers and I occasionally get free products to post about. Could the vet bills be a business expense if he's technically generating income?

That's actually a great question about social media pets. It could potentially qualify if you've properly set up a business entity and your pet's social media presence generates regular income that you report on your taxes. You'd need to treat it like a legitimate business with proper bookkeeping showing the connection between the pet's health and your business income. If you're only occasionally receiving free products but not actually reporting income from this activity, it would be much harder to justify as a business expense. The IRS looks for regular, ongoing business activity with the intent to make a profit, not just hobby activities.

Your accountant gave you incorrect information. FSAs and HSAs are specifically for qualified human medical expenses only. Using these accounts for pet expenses would violate IRS rules and could result in penalties. You might want to double-check this with another tax professional.

Do you know if you can claim this refund if you're not required to file a US tax return otherwise? I'm in a similar situation (small dividend after moving) but don't have any other US income to report.

Yes, you can still claim a refund even if you're not otherwise required to file a US return. You would file Form 1040-NR specifically to claim the refund of overwithholding. For small amounts, you'll need to decide if it's worth the effort. The form isn't particularly complicated, but you'll need to include a copy of your 1042-S showing the withholding and explain that you're eligible for the lower treaty rate. Some people find it's not worth the hassle if the refund amount is very small.

This is a good point. Would the broker still provide an accurate cost basis on the 1099-B for those reinvested shares even if the account holder is now a non-resident alien?

That's a really good point about local taxes - I hadn't even considered that yet. Do you know if Florida has any significant local taxes I should be watching for? Also, what exactly is an "annual report requirement"? Is that different from the tax filing itself?

Florida doesn't have many problematic local taxes that apply to out-of-state businesses, so you're fairly lucky there. Some counties have their own small business taxes, but they typically only apply if you have physical presence in that county. Annual reports are separate from tax filings. Once you register to do business in a state (called "foreign qualification"), most states require you to file an annual report and pay a fee to maintain your good standing. It's basically just confirming your business information is current and paying to maintain your authorization to do business there. In Florida, it's due by May 1st each year, and the fee varies based on your entity type. If you forget to file these reports, some states can administratively dissolve your registration, which can affect your ability to sue in that state or access their court system.

Which states did this happen in? I'm in a similar situation and trying to avoid surprises!

That's a really good point about state taxes that I hadn't considered. I'm in Texas which doesn't have state income tax, but we did live in California for two years during our marriage. Should I be concerned about that?

Yes, absolutely contact California's tax authority (Franchise Tax Board) immediately! California is extremely aggressive about collecting back taxes, and they have a lookback period of up to 20 years for tax fraud. If your ex didn't pay proper taxes while you lived there, California could come after you separately from the IRS. California does have an innocent spouse program, but you need to be proactive about it. Don't wait for them to find you. The good news is that if you get innocent spouse relief from the IRS, California generally follows the federal determination, but you still need to file the proper paperwork with them.

Adding to this excellent advice - be prepared for a long process. My innocent spouse case took 14 months to resolve completely. The IRS isn't known for speed. Make sure you respond to every letter they send within the timeframe they specify, and always send things certified mail so you have proof of delivery.