This thread has been incredibly helpful! I was pulling my hair out over the same issue with my Schwab 1099-B. I kept seeing gain/loss calculations right there on the form but getting warnings about missing cost basis info. After reading through everyone's explanations, I finally understand that it's all about what gets reported to the IRS versus what the brokerage shows me. The key insight about checking the "Cost Basis Reported to IRS" column on the 1099-B is gold - I wish they made that more obvious! For anyone else dealing with this, I found that most of my "non-covered" transactions were from stock purchases I made back in 2009-2010 (before the reporting requirements kicked in) and some transfers from an old Merrill account. Makes total sense now why those would need code B on Form 8949 even though Schwab calculated the gains correctly on my form. One thing I'd add is that if you're using tax software, double-check that it's not automatically importing these as "covered" transactions. I caught TaxAct trying to treat everything as if it was reported to the IRS, which would have been wrong for about half my trades.

I've been dealing with this exact same confusion for years and finally have a system that works! What really helped me was creating a simple spreadsheet to track the status of each transaction before tax season even starts. Here's what I do: Every time I sell something, I immediately check Fidelity's "Positions" page to see if that security shows up as "covered" or "non-covered" for cost basis reporting. I log this in my spreadsheet along with the basic transaction details (date sold, proceeds, my calculated gain/loss). Then when my 1099-B arrives, I can quickly cross-reference my spreadsheet against the "Cost Basis Reported to IRS" column to make sure everything matches up. Any "No" entries in that column go straight to the "needs code B on Form 8949" pile. This has saved me so much stress during tax season because I'm not scrambling to figure out which transactions are causing the "missing cost basis" warnings. Plus it helps catch any discrepancies between what I calculated during the year versus what shows up on the actual 1099-B. The whole system takes maybe 5 minutes per transaction when I sell, but saves hours of confusion in March/April!

Something no one mentioned yet - if you live in a state with income tax, you'll likely owe state taxes on gambling winnings too! Each state has different rules. For example, some states allow you to deduct losses like federal, others don't. Make sure you check your specific state's rules.

One thing that might help ease your mind - the $600 threshold is just a reporting requirement, not a withholding trigger. Most sports betting platforms won't automatically withhold taxes from your winnings unless you hit much higher thresholds (usually $5,000+ and certain odds ratios). However, you're still responsible for paying taxes on ALL your gambling income when you file, regardless of whether taxes were withheld. Since you're expecting to stay under $5,000 for the year, you probably won't have automatic withholding, but you should set aside about 20-25% of your net winnings to cover federal and state taxes. Also, make sure you understand the difference between gross winnings and net winnings. You can only deduct losses up to your total winnings if you itemize deductions, so if you win $4,000 but lose $3,000, you'd pay taxes on the full $4,000 but could potentially deduct the $3,000 in losses. Keep every receipt and record!

I had the exact same issue last year! I used H&R Block, uploaded Form 8332 for my daughter, and was told they'd mail the 8453. Six months later, my ex got a letter from the IRS saying the dependency exemption was denied because they never received the form. When I went back to H&R Block, they admitted they "couldn't find any record" of mailing it. I ended up having to file an amended return and mail everything myself with certified mail. H&R Block did cover the fees for the amendment since it was their mistake, but it was a huge hassle. Definitely don't just trust that they're handling it!

This is such a frustrating situation that unfortunately happens more often than it should. I work as a tax compliance specialist and see this exact issue regularly. Here's what you need to know: 1. **Immediate action needed**: Don't wait any longer. Contact H&R Block's office manager (not just any employee) and demand written confirmation that your Form 8453 with attached Form 8332 was mailed, including the date and IRS processing center address. 2. **If they can't provide proof**: Mail the forms yourself immediately with certified mail. You can still submit Form 8332 even after the original return was filed - just include a cover letter explaining the situation. 3. **Timeline matters**: The IRS typically processes these within 6-8 weeks once received. If your ex filed claiming the dependency exemption without the supporting form, his return might be in "pending" status or he could receive a notice requesting the documentation. 4. **Protect yourself**: Going forward, always request a copy of Form 8453 and tracking confirmation for any mailed documents. Many preparers are supposed to provide this automatically but don't always follow through. The good news is this can still be fixed, but time is critical. Don't let H&R Block's confusion delay your action any further.

Has anyone here dealt with selling a Treaty of Amity company? I'm considering buying one from another American, and wondering about tax implications of the purchase/sale transaction.

This is such a helpful thread! I'm in a similar situation - American looking to start a business in Thailand under the Treaty of Amity. Reading through all these responses, it sounds like the key takeaways are: 1) It's a Thai company with special ownership privileges, not a US company 2) Form 5471 is definitely required for CFC reporting 3) FBAR and Form 8938 likely needed for bank accounts 4) GILTI and Subpart F rules can apply 5) FEIE is still possible but gets complicated with company ownership One question I haven't seen addressed - does the type of business matter for these reporting requirements? I'm looking at starting a consulting business vs. my friend who wants to do e-commerce. Would both have the same IRS filing obligations, or do certain business types trigger additional requirements under the Treaty of Amity structure? Also, has anyone worked with a US tax professional who specializes in Treaty of Amity businesses? It seems like regular expat tax preparers might not be familiar with this specific structure.

Has anyone dealt with currency conversion issues when reporting foreign property sales? I sold a house in Europe last year and the exchange rate fluctuated like crazy between when I inherited it, when I sold it, and when I transferred the money. My tax guy said I needed to use the exchange rate on the day of the sale for reporting capital gains, but use a different method for basis calculation?

This is a complex situation that definitely requires careful handling! One thing I haven't seen mentioned yet is the importance of getting proper documentation of the property's fair market value at the time of inheritance. Your cousin will need this for the stepped-up basis calculation everyone's discussing. I'd strongly recommend he get an official appraisal or valuation from the foreign country dated as close as possible to when his mother passed away. Without proper documentation of the stepped-up basis, the IRS might challenge his calculations and assume a much lower basis (or even zero), which would result in much higher taxes. Also, since he's bringing $300k into the US, he should be aware of the requirement to report large cash transfers. If he's wiring the money or bringing in more than $10,000 in monetary instruments, there are additional reporting requirements beyond just the tax return. Given all the complexities with foreign property, dual citizenship, currency conversion, and multiple forms (Schedule D, 8949, FBAR, possibly 8938), I'd really encourage him to work with a tax professional who specializes in international tax issues. The potential penalties for getting this wrong are significant, and the cost of professional help is usually much less than the cost of mistakes.