Do you know how I can specifically request this first-time penalty abatement? Would I need to call the IRS directly or is there a form? We've never had issues before these last two years so maybe we qualify.

You can request first-time abatement by calling the IRS directly - there's no specific form for it. When you call, specifically ask for "first-time penalty abatement" under the IRS First Time Abatement policy. Be prepared to verify that you haven't had penalties in the prior 3 tax years. Alternatively, you can write a penalty abatement letter after you receive a bill with penalties. Include your name, address, SSN, and a statement requesting first-time abatement. Make it clear you've had a clean compliance history and are taking steps to avoid future issues (like updating your W4s, which you've already done).

This could be dangerous advice depending on the person's credit situation. IRS interest rates (currently around 7-8%) are often lower than credit card rates after promotional periods (often 18-25%). If they can't pay off the card in time, they'd be in worse shape.

That's a really good point I hadn't considered! He is a full-time college student, so I think I'm still eligible to claim him. He works part-time at the campus bookstore, but I'm definitely providing well over half his support (tuition, housing, food, car insurance, phone, etc.). Do you know if there's any form or documentation I should get from his college to prove he's enrolled full-time? I want to make sure I have everything in order before this becomes an issue with the IRS.

You'll want to get a transcript or enrollment verification from his college showing his full-time status for the tax year. Most schools can provide this through their registrar's office or student portal. This is important documentation to have on hand. For the support test, keep records of all those expenses you mentioned. Create a spreadsheet showing what you pay versus what he earns from his job to clearly demonstrate you provide more than half his support. Also, make sure you understand the difference between the Qualifying Child and Qualifying Relative tests for dependents - at 19, he's only a Qualifying Child if he's a full-time student, otherwise you'd need to see if he meets the tests for a Qualifying Relative.

This is what I was thinking too. At 19, why isn't the son just providing his own SSN to his parent? Something seems off about this whole situation. Maybe there's more to the story?

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?