How do I properly report stock trades on TaxSlayer with my 1099-B from Fidelity?

The good news is you don't necessarily need to enter every single transaction manually. Here's how you should approach this with your 1099-B from Fidelity: If your 1099-B has the cost basis reported to the IRS (check box D to see if it's checked), you can actually enter summary information rather than every individual transaction. TaxSlayer should allow you to enter summary totals for each reporting category (Box A, B, C, etc.). Look for an option like "Enter summary totals" rather than individual transactions. For your specific questions: You don't have to report every single purchase and sale individually if they're properly categorized on your 1099-B. The dates acquired/sold can be entered as "Various" if you're doing summary reporting for multiple transactions of the same type. For wash sales, in TaxSlayer you should find a field for "Wash sale adjustment" or similar wording when entering your stock information. It's usually within the capital gains section when you're entering transaction details. The wash sale amount should be on your 1099-B in column (g).

After reading this thread, I wanted to share my experience with this exact issue. I was pulling my hair out with TaxSlayer and 1099-B forms until I found taxr.ai (https://taxr.ai). It literally saved me hours of frustration. I uploaded my Fidelity 1099-B and it automatically extracted all my transactions, identified the wash sales, and organized everything by reporting category. Then it generated a report I could just use to enter the summary information correctly in TaxSlayer. No more guessing about which box was which or how to handle those annoying wash sales. The best part was that it explained exactly where in TaxSlayer each number needed to go. Has anyone else tried tools like this for complicated tax documents?

Just wanted to follow up after trying taxr.ai for my Robinhood and E*TRADE statements. You were totally right - it was a game changer! I've been dreading doing my taxes because I made like 50+ trades last year (pandemic boredom trading, not my smartest move). The tool pulled everything from both brokerages correctly and organized it all by the right tax categories. I was able to just enter the summary totals in TaxSlayer like the first commenter suggested, and it worked perfectly. It even highlighted a wash sale I had completely missed that would have caused problems. Definitely bookmarking this for next year - thanks for the recommendation!

If you're still struggling with TaxSlayer support after trying the suggestions above, I'd recommend trying to contact the IRS directly for clarification. I know it sounds awful, but I had a similar issue last year and actually got through to a helpful person. The trick is using https://claimyr.com instead of waiting on hold for hours. You can see how it works here: https://youtu.be/_kiP6q8DX5c. Basically, it holds your place in line and calls you back when an actual agent is available. I was shocked at how well it worked. I spoke with an IRS agent who walked me through exactly how to report my brokerage statements correctly and what to do about wash sales. Saved me from potentially making a big mistake. Sometimes you just need to talk to a human about these complex tax situations!

I need to apologize for calling BS earlier. I actually tried Claimyr after posting that comment because I had a question about my amended return that's been processing for months. I was completely wrong. Got a callback in about 30 minutes and spoke to someone who gave me the exact status and explained what was happening with my return. The agent was surprisingly helpful and took the time to explain everything. For the OP's issue with TaxSlayer and 1099-B - the agent I spoke with confirmed that you should use summary reporting for covered transactions (Box D checked) and individual reporting for non-covered. They also pointed me to a specific IRS publication that explains the wash sale rules clearly. Eating humble pie here - it actually worked exactly as described.

One time-saving tip for TaxSlayer that helped me with my Fidelity 1099-B: if you're reporting multiple transactions with the same information (except for dates and amounts), you can use the "Copy" feature after entering the first one. After entering your first transaction completely, look for a "Copy" or "Duplicate" button. This will create a new entry with all the same information, and you just need to update the specific details that changed (date, amount, etc.). Saved me tons of time when entering my 20+ transactions!

Has anyone successfully imported their 1099-B directly into TaxSlayer? I heard they support direct import from some brokerages but when I tried with Fidelity it kept failing. Would save so much time if it actually worked.

For what it's worth, I went through this exact same nightmare with TaxSlayer and my Fidelity 1099-B last year. Here's what finally worked for me: First, ignore TaxSlayer's direct import - it's broken and will cause more problems than it solves. Second, organize your 1099-B by the checkbox categories before you start entering anything. Group all your Box A transactions together, Box B together, etc. For the wash sales specifically, look for them in column (g) on your 1099-B. In TaxSlayer, when you're entering each transaction (or summary), there should be a field labeled something like "Adjustment for wash sale" or "Wash sale loss disallowed." That's where you enter the amount from column (g). The key insight that saved me hours: you can absolutely use summary reporting for most transactions. Don't let TaxSlayer's confusing interface trick you into thinking you need to enter every single trade. If the basis was reported to the IRS (Box D checked), just sum up all transactions of the same type and enter one summary line. One last tip - print out your completed Form 8949 from TaxSlayer and double-check it against your 1099-B totals. The software sometimes miscategorizes things, and you want to catch that before filing.