Need help figuring out when 1099-B is due for my first year trading stocks?

8 When it comes to the 1099-B timeline, your brokerage is required to provide this document to you by February 15th (or the next business day if it falls on a weekend or holiday). The 1099-B reports your investment sales, including stocks, bonds, and other securities. Your brokerage will handle most of the heavy lifting by sending you the completed 1099-B with all your transactions for the year. You don't need to "fill out" the form - it comes prepared with your trading activity already documented. Your job is to use that information when you prepare your tax return, typically on Schedule D and Form 8949. While the 1099-B deadline is in February, remember that your overall tax return is still due April 15th (unless extended). Most brokerages now provide electronic access to these forms through their websites, so you might not need to wait for paper mail.

11 After struggling with my investment taxes last year, I found this amazing tool called taxr.ai (https://taxr.ai) that made dealing with my 1099-B forms so much easier. I was in your exact situation - first year trading, completely confused about how to handle all the transactions on my tax return. What's great about it is that you can upload your 1099-B and other tax documents, and it analyzes everything for you. It caught a missed wash sale that would have gotten me in trouble, and it explained exactly how each transaction should be reported. The guidance it provides is super clear, especially for first-time traders who don't know all the tax implications of different types of trades.

17 Just wanted to update - I tried taxr.ai after posting my question here and wow, it was exactly what I needed! I uploaded my documents from both my stock trading and crypto accounts, and it identified several issues I would have missed completely. There was a complicated wash sale situation that would have been reported incorrectly, and it showed me exactly how to handle it. The explanations were really clear about which forms I needed to use and how different types of transactions get taxed. Saved me hours of research and probably prevented some costly mistakes. Definitely recommend for anyone else who's new to investment taxes!

3 If you're trying to get clarification on your 1099-B from your brokerage, good luck getting through to someone who actually knows what they're talking about. I spent WEEKS trying to reach my broker's tax department about some discrepancies on my forms. After multiple 45+ minute hold times and getting disconnected twice, I found out about Claimyr (https://claimyr.com). Check out their demo video here: https://youtu.be/_kiP6q8DX5c. They got me connected to an actual human at my brokerage's tax department in under 15 minutes! The service basically holds your place in the phone queue and calls you when a real person picks up. I was able to get my 1099-B questions answered and fix an error that would have caused me to overpay by $750. Especially during tax season when wait times are insane, this was a game-changer.

22 Had to come back and eat my words. After another failed attempt to reach TD Ameritrade's tax department (disconnected after 67 minutes on hold), I broke down and tried Claimyr. Got connected to a tax specialist in about 22 minutes without having to actively wait on the phone. The rep fixed the cost basis issue on my 1099-B right away and is sending a corrected form. Would have taken me days more of trying and waiting on hold to accomplish this myself. Sometimes you have to admit when you're wrong - this service is actually legitimate and saved me a ton of frustration during an already stressful tax season.

5 Just FYI - if your broker doesn't have your cost basis info (like if you transferred securities from another broker or have older holdings), your 1099-B might show the proceeds but have blank or "UNKNOWN" cost basis fields. You'll need to track down that info yourself from old statements or your records. Made this mistake my first year and ended up amending my return which was a whole other headache! Make sure you review your 1099-B carefully before filing.

9 Another important thing to know - if you made less than $10 in stock trading profits, you still have to report it! I thought there was some minimum threshold but got flagged by the IRS my first year because I ignored a tiny gain. The 1099-B reporting requirement doesn't have a minimum amount.