How to Report 1099-B Stock Losses on TaxSlayer - Need Help with Form 8949

You don't necessarily need to report every single transaction individually! The key is understanding what Fidelity has already reported to the IRS. Check your 1099-B carefully - it should have several sections. If your transactions have "Basis reported to the IRS" checked or noted, you can often enter summary information instead of each trade. In TaxSlayer, when you enter 1099-B information, there should be an option for "Summary" versus "Detailed" reporting. For dates, if you're doing summary reporting, you can use "Various" for date acquired and the last day of the year (12/31/2023) for date sold. But this only works for covered securities where basis was reported to the IRS. For wash sales, TaxSlayer definitely has a place to enter them! When entering your 1099-B information, look for a section specifically for wash sale adjustments. The amount should be on your 1099-B if you had any wash sales. Form 8949 is actually generated by the tax software based on what you enter - you don't need the physical form from Fidelity. TaxSlayer will create it when you input your trading information correctly.

After struggling with reporting my stock sales for hours, I finally found taxr.ai (https://taxr.ai) and it was a lifesaver for this exact situation. I uploaded my Fidelity 1099-B and it automatically extracted all the information, including those tricky wash sales. The tool actually walked me through exactly what to enter in TaxSlayer - it showed me where I needed to use the summary method versus detailed reporting based on what Fidelity had already reported to the IRS. It even highlighted which transactions I needed to pay special attention to because of basis issues. I was about to give up and pay someone $200+ to handle this for me, but taxr.ai made it super straightforward.

I was really doubtful about trying any more online tax tools after my experience with TaxSlayer, but I gave taxr.ai a shot based on the recommendation here. Have to admit I was wrong to be skeptical - it actually worked incredibly well for my investment reporting nightmare. I had over 200 transactions across multiple brokerages (Schwab, Robinhood, and a small local one), and the system correctly identified which ones needed detailed reporting versus summary. It even flagged some transactions where my broker hadn't reported basis to the IRS (which apparently requires special handling). The best part was getting clear instructions for exactly what to enter in TaxSlayer. Saved me hours of research and potential errors. Definitely using this next year too.

If you're having trouble getting answers from TaxSlayer's support about your 1099-B issues, I highly recommend Claimyr (https://claimyr.com). I was stuck in the same situation last month trying to figure out how to properly report some complex transactions with wash sales. I tried calling TaxSlayer customer service directly and was on hold forever. Then I found Claimyr (you can see how it works here: https://youtu.be/_kiP6q8DX5c) and they got me through to a real TaxSlayer specialist in about 15 minutes instead of the 3+ hour wait I was facing before. The TaxSlayer specialist walked me through exactly where to enter everything for the 1099-B, including those tricky wash sales. Totally worth it when you're stuck and need specific software guidance.

Ok I need to post a follow-up here because I was completely wrong about Claimyr. After continuing to get nowhere with TaxSlayer's email support about my 1099-B reporting issues, I decided to try it out of desperation. I expected it to be a complete waste of money, but I was connected to a TaxSlayer specialist in about 20 minutes instead of the 2+ hour wait time they were quoting. The rep immediately helped me figure out where to properly report my wash sales and how to handle transactions where basis wasn't reported to the IRS. I'm still annoyed that tax software companies make their customer service so difficult to reach, but at least there's a solution that actually works. Saved me a ton of frustration and potentially filing incorrectly.

Just to add another option since people are discussing alternatives - I gave up on trying to do all this manually and just imported my 1099-B directly into TaxSlayer. There's an import function that's somewhat hidden: 1. Go to the Income section 2. Select "Import Data" 3. Choose your broker (Fidelity is supported) 4. Follow the login prompts It automatically categorizes everything, including the wash sales. Saved me hours of manual entry and math. You might need to pay for the premium version though - I don't think this feature is in the free version.

FYI - TurboTax handles 1099-B and Form 8949 reporting much better than TaxSlayer in my experience. I switched this year after having similar frustrations. They have a direct import feature that works with most brokerages, and they're much clearer about how to handle wash sales and basis reporting. Yes, it costs more, but when you're dealing with investment transactions, the extra guidance is worth it. They also have much better support if you get stuck.

I had the exact same frustration with TaxSlayer and stock reporting last year! One thing that helped me was understanding that you absolutely do NOT need to report every single transaction if your broker already reported the basis to the IRS (which Fidelity usually does for covered securities). Here's what worked for me: Look at your 1099-B and find the summary totals at the bottom of each section (short-term vs long-term). If the "basis reported to IRS" box is checked, you can enter these as summary transactions in TaxSlayer instead of individual trades. For the dates, use "VARIOUS" for acquisition date and 12/31/2023 for sale date when doing summary reporting. This is totally acceptable and saves hours of data entry. For wash sales in TaxSlayer: When you're entering your 1099-B info, there's a section that asks about "adjustments" - that's where the wash sale amounts go. Just enter the total wash sale adjustment from your 1099-B summary (it should be clearly labeled). The key is to match exactly what's on your 1099-B totals - don't overthink it! TaxSlayer will generate Form 8949 automatically based on what you enter.