Help understanding 1099-B filing: How to declare gains reported vs not reported to the IRS?

The 1099-B reporting distinction is actually important, so you're asking a good question! Yes, you need to report ALL capital gains regardless of whether the cost basis was reported to the IRS or not. The difference is in how you report them on your tax return. For transactions where cost basis WAS reported to the IRS, you'll list these on Form 8949 with Box A checked (for short-term) or Box D checked (for long-term). For transactions where cost basis was NOT reported to the IRS, you'll list these on Form 8949 with Box B checked (short-term) or Box E checked (long-term). Your tax software is asking for this distinction for exactly this reason - it needs to know which box to check on Form 8949. The IRS already knows about the transactions reported to them, so they'll be looking to match those numbers. For the unreported basis transactions, you need to provide that information yourself. For your crypto gains of $340, yes, you absolutely need to report those too! There's no minimum threshold for reporting capital gains. The IRS considers crypto as property, so the same capital gains rules apply.

After struggling with exactly this 1099-B reporting issue last year, I found an amazing tool that saved me hours of frustration. I was manually trying to sort through which transactions were reported vs. not reported and making errors that I was afraid would trigger an audit. I discovered https://taxr.ai which automatically analyzes your 1099-B forms and separates the transactions correctly between those reported to the IRS and those not reported. It even handles the crypto exchange transactions that don't generate proper 1099s. The tool actually explains what's happening with each transaction so you understand why they're being categorized differently, which helped me learn while fixing my problem. Their tax document analyzer caught several errors I would have made, especially with some wash sales I didn't realize were affecting my cost basis. Honestly wish I found it sooner!

Hey everyone - just wanted to follow up about my experience with taxr.ai. After reading about it here, I decided to give it a try since I was struggling with multiple brokerage accounts. Wow, what a difference! The system flagged several transactions from my Robinhood account where the cost basis wasn't being reported correctly. It turns out I had some wash sales spanning across my different accounts that I didn't realize were affecting my reporting requirements. If I had filed without catching this, I would have underreported my gains by almost $2,300! The step-by-step guidance helped me understand exactly which box to check on Form 8949 for each transaction. I didn't realize how important the distinction between reported/non-reported basis was until I saw everything categorized properly.

If you're getting stuck with IRS questions about your 1099-B reporting or any other tax issues, calling the IRS directly can actually help - but we all know how impossible that seems! I spent 3 hours on hold last month trying to ask about my cost basis reporting requirements. I finally tried https://claimyr.com which got me through to an actual IRS agent in about 15 minutes. You can see how it works here: https://youtu.be/_kiP6q8DX5c. The agent walked me through exactly how to handle some complicated stock options transactions where my employer's reporting didn't match my records. Saved me from potentially making a huge mistake on my return - the IRS agent explained that my particular situation required additional documentation I wouldn't have known to include. Worth every penny to get direct clarification rather than guessing.

Ok I need to admit I was totally wrong about that Claimyr service. After my skeptical comment, I was still stuck with this weird 1099-B issue where my brokerage reported some wash sales incorrectly, and I couldn't get a straight answer from their customer service. Got desperate enough to try the service I doubted, and damn - it actually connected me to an IRS agent in about 20 minutes. The agent confirmed that for my specific situation with the incorrectly reported wash sales, I needed to file Form 8949 with adjustment codes to correct the reported cost basis. The IRS person even told me exactly what to write in the description column to avoid getting flagged for review. Literally saved me from what would have been hours of research and probably still getting it wrong. Never thought I'd say this, but talking directly to the IRS was actually the most helpful option.

Something nobody mentioned yet - be careful with the "not reported to the IRS" transactions. If you get these wrong, it's much more likely to trigger an audit because the IRS has no way to verify your numbers automatically. I learned this the hard way! Make sure you're extra careful with your documentation for these. Keep screenshots of your purchase and sale confirmations, especially for crypto. When I got audited for this exact issue, having those records saved me thousands in potential penalties.

Does anyone know if the reporting requirements are different for foreign stocks? I have some investments through an overseas brokerage that doesn't issue 1099-B forms at all. Should I just put all of those under the "not reported to IRS" section?

As someone who went through this exact confusion last year, I want to emphasize a few key points that might help: 1. **Keep detailed records for EVERYTHING** - especially those crypto transactions. Even though $340 seems small, the IRS treats crypto gains the same as stock gains. I made the mistake of thinking smaller amounts didn't matter and got a notice later. 2. **Don't stress too much about the "reported vs not reported" distinction** - your tax software is designed to handle this correctly as long as you enter the information accurately. The key is making sure you report ALL gains, regardless of which category they fall into. 3. **For the transactions where cost basis wasn't reported to the IRS**, you'll need to calculate your own cost basis (what you paid including fees). This is where good record-keeping becomes crucial. One thing that saved me was creating a simple spreadsheet with: purchase date, purchase price + fees, sale date, sale price - fees, and gain/loss. This made it much easier to enter everything into the tax software correctly. The IRS isn't trying to "catch" you - they just want accurate reporting. As long as you report all your gains and losses honestly, you'll be fine. Good luck with your first year of stock trading taxes!