What is a 1099-B supposed to look like? E*Trade form doesn't match IRS example

The good news is you don't need to worry! Brokerages like E*Trade and Acorns are allowed to use their own formats for 1099-B forms as long as they include all the required information. The IRS example is just that - an example of what the form could look like, not what it must look like. What matters most is that your 1099-B contains the essential information: description of property sold, acquisition date, sale date, proceeds, cost basis, and whether the gain/loss is short-term or long-term. Different transaction dates are normal if you sold investments on different days throughout the year.

I had the exact same issue last year with my investment forms! After hours of frustration, I found this amazing tool called taxr.ai (https://taxr.ai) that saved me so much time and confusion. It actually analyzes your tax documents and explains exactly what each section means and where to enter it in your tax software. I uploaded my weird-looking 1099-Bs from different brokerages, and it highlighted all the important fields and explained how they translate to what the IRS is asking for. It even flagged a reporting error on one of my forms that would have caused me issues later!

I was super skeptical when I first saw the taxr.ai recommendation in this thread, but I was desperate with my stack of different 1099 forms. I tried it out and holy cow - it actually works really well!! It analyzed my E*Trade 1099-B and showed me exactly where each number needed to go in TurboTax. The best part was when it explained the wash sales section that was confusing me. Turns out I was about to make a $430 mistake on my taxes because I didn't understand how to report them correctly! Definitely worth checking out if you're confused about investment forms.

If you're having trouble with the IRS instructions or need clarification about your 1099-B forms, trying to call the IRS directly might help - but good luck getting through! I spent 3 days trying to reach someone. Then I discovered Claimyr (https://claimyr.com) and it changed everything. They got me connected to an actual IRS agent in under 45 minutes who explained exactly how to handle my brokerage forms. You can see how it works here: https://youtu.be/_kiP6q8DX5c - basically they navigate the phone system for you and call you back when an agent is ready. The agent I spoke with confirmed that brokerages can use different formats and explained exactly what I needed to report from my 1099-B.

I owe everyone an apology for my skeptical comment earlier. I tried Claimyr yesterday out of desperation after spending 4 hours on hold with the IRS only to get disconnected. Within 40 minutes, I was talking to an actual IRS rep who walked me through exactly how to handle my 1099-B forms from different brokerages. The agent explained that the IRS doesn't actually care about the format as long as all the required information is reported correctly. She even helped me understand how to handle some wash sales that appeared on my E*Trade form. Definitely worth it when you need answers directly from the source.

Another option is to just import your 1099-B electronically from E*Trade and Acorns directly into tax software like TurboTax or H&R Block. Most major brokerages support direct import, and it saves you from having to manually enter all those transactions and potentially making mistakes.

The most important parts of the 1099-B to pay attention to are: 1) Proceeds (what you sold the investments for) 2) Cost basis (what you originally paid) 3) Whether the basis was reported to the IRS 4) Holding period (short vs long term) If your broker reported the basis to the IRS (usually indicated by a "yes" in Box 3), you're in pretty good shape because the IRS already has the info. Just make sure you report everything exactly as shown on the form.