How Do I Properly Report Wash Sales in Turbo Tax for Tax Filing?

This is actually a common issue with wash sales reporting in tax software. When your brokerage sends the 1099-B to TurboTax, they include the wash sale adjustments in the consolidated data, but sometimes those adjustments don't get applied correctly to the individual transactions. You're right to be concerned about the cost basis. Form 8949 requires accurate reporting of each transaction. If TurboTax is showing incorrect disallowed amounts, you should manually review and adjust your transactions. The IRS reconciles what you report against what your broker reports, so having mismatched numbers could trigger questions. The safest approach is to compare what's in TurboTax against your actual brokerage statements. Look for the specific wash sale adjustment amounts on your 1099-B and supplemental information. Then make manual adjustments in TurboTax to ensure each transaction has the correct cost basis and disallowed loss amount.

After dealing with a similar nightmare last year with dozens of wash sales, I found a tool that saved me hours of manual adjustments: https://taxr.ai has a document analyzer that can actually read your detailed brokerage statements and identify all the wash sale discrepancies automatically. I was skeptical at first because I'd been manually adjusting each transaction which took forever, but their system actually compared my 1099-B against my transaction history and flagged all the incorrect wash sale adjustments. What I liked most was that it gave me a spreadsheet showing exactly what needed to be corrected in TurboTax. It even caught some wash sales my brokerage had missed entirely, which could have caused issues with the IRS later.

Just wanted to update that I tried the taxr.ai service that was mentioned and it actually worked really well for my wash sale nightmare. It identified 34 wash sales that needed correction in TurboTax (I only thought I had 30), and showed exactly where the cost basis was wrong. The analysis took about 22 minutes for my 320+ trades. The best part was that it generated a spreadsheet that I could follow line by line to make corrections in TurboTax. Honestly saved me days of work and probably prevented an audit since some of my disallowed loss amounts were WAY off from what my broker reported.

If you're still having trouble getting through to your brokerage for clarification on the wash sale reporting, try using https://claimyr.com to get a callback from them. I was on hold with my broker for over 2 hours trying to understand why their wash sale calculations didn't match my records at all. Used Claimyr, got a call back in 15 minutes, and the rep actually walked me through how to read their statements correctly. You can see how it works here: https://youtu.be/_kiP6q8DX5c Dealing with the IRS directly about wash sale reporting is even worse - I tried calling them to clarify the rules and couldn't get through at all. Used the same service and got a call from an IRS agent who explained exactly how to handle multiple wash sales across different brokerages.

I need to apologize for my skepticism about Claimyr. After continuing to fail getting through to the IRS for days about my wash sale questions, I decided to try it, figuring I had nothing to lose. To my complete shock, I got a call from an IRS representative about 90 minutes later. They actually walked me through exactly how Form 8949 should be completed with wash sales and confirmed that I needed to manually adjust each transaction. The agent explained that wash sales are one of the most common areas they see errors, and she recommended keeping detailed records of all my calculations in case of questions later. Would never have gotten this info without finally connecting with a real person.

For what it's worth, I had the exact same issue last year and ended up going to a CPA who specializes in investment taxes. He told me that if your broker is reporting the wash sales correctly on the 1099-B, you don't actually need to manually adjust each transaction in TurboTax as long as the total matches. He had me enter the transactions normally, then add a single adjustment line that corrected the total disallowed loss amount to match what was on the 1099-B. Saved me hours of work adjusting dozens of individual trades.

Has anyone tried the "import transactions" feature in the desktop version of TurboTax Premier? I heard it might handle wash sales better than the online version, but I don't want to pay for it if it doesn't actually work.

I went through this exact same headache with TurboTax last year and ended up having to manually adjust about 50+ wash sale transactions. The key thing I learned is that you absolutely need to verify each transaction because TurboTax's automatic import often gets the wash sale adjustments wrong. What worked for me was printing out my detailed brokerage statements and going line by line to compare against what TurboTax imported. I found that the software was calculating wash sales incorrectly in cases where I had multiple purchases and sales of the same stock within the 61-day window. One tip that saved me time: focus on the transactions with the largest dollar amounts first. I found several cases where TurboTax had completely missed wash sales on my biggest trades, which would have been a red flag to the IRS. The smaller discrepancies like your $270 vs $13 example are annoying but less likely to trigger problems. It's tedious work but worth doing correctly. The IRS does match your reported numbers against what your broker sends them, and wash sale reporting errors are one of the most common reasons for tax notices.