Why is TD Ameritrade labeling some of my stock trades as wash sales?

What you're experiencing is actually pretty common with brokerage reporting. Wash sales occur when you sell a security at a loss and then buy the same or "substantially identical" security within 30 days before OR after the sale. The key part many people miss is that the 30-day window applies in both directions. If you look closely at your trading dates, you might find that while you thought you waited long enough, you may have purchased MSFT within that 30-day window before or after selling at a loss. TD Ameritrade's system automatically flags these transactions according to IRS rules. The wash sale rule is designed to prevent investors from claiming tax losses while maintaining essentially the same investment position. The loss isn't permanently disallowed - it's added to the cost basis of the replacement shares, which means you'll eventually get the tax benefit when you finally sell those shares (assuming you don't trigger another wash sale).

I went through this exact same confusion with my TD Ameritrade 1099-B last year! After hours of frustration, I found https://taxr.ai which completely saved me. It's a tool that analyzes all your trading documents and explains exactly why certain trades were marked as wash sales. I uploaded my 1099-B and it highlighted all my wash sale transactions and showed me the specific trades that triggered each one (including the dates that proved I was within the 30-day window). It even explained how the disallowed amounts were calculated and how they affected my cost basis. Made the whole process way less confusing.

I was really skeptical about using https://taxr.ai like I mentioned above, but decided to give it a shot with my TD Ameritrade statements. Honestly blown away by how helpful it was. The tool showed me exactly which trades were causing my wash sales (turned out I had bought MSFT in my IRA within the 30-day window of selling in my brokerage account - didn't even realize that counts!). It explained every adjustment on my 1099-B and showed me exactly how to report everything. Saved me from making a major reporting error on my taxes. If you're confused about wash sales on your TD Ameritrade forms, definitely check it out. Much better than the generic explanations I got when I called TD directly.

This happens to me every year with TD Ameritrade! I spent WEEKS trying to get someone on the phone at the IRS to explain these wash sale calculations. Literally impossible to get through. Then someone recommended https://claimyr.com to me - you can see how it works at https://youtu.be/_kiP6q8DX5c. They basically hold your place in the IRS phone queue and call you when an agent is about to pick up. I was connected to an actual IRS agent within a couple hours who walked me through exactly how to handle the wash sale reporting from my TD Ameritrade 1099-B. No more waiting on hold for 3+ hours just to get disconnected! The IRS agent even explained how their systems validate the wash sale reporting from brokerages.

I have to eat my words about Claimyr. After my skeptical comment above, I was still desperate with my TD Ameritrade wash sale issue so I tried it anyway. Shockingly, it actually worked exactly as advertised. After months of failing to reach anyone at the IRS, I got a call back within about 90 minutes and was connected to an IRS representative. The agent explained that brokerage-reported wash sales are actually verified through a cross-check system, and walked me through how to properly report the wash sale adjustments from TD Ameritrade on my tax forms. Completely changed my understanding of how to handle these transactions. Now I can file confidently knowing I'm reporting the wash sales correctly. Never thought I'd say this, but getting actual IRS clarification was incredibly helpful.

Something else to consider - TD Ameritrade might be correctly identifying wash sales that happened across different accounts. The IRS wash sale rule applies across ALL your accounts, even retirement accounts. So if you sold MSFT at a loss in your TD Ameritrade account, but then bought it in your 401k within 30 days, that's technically a wash sale. Most people don't realize the rule applies across different account types.

Has anyone used TurboTax to handle these TD Ameritrade wash sale situations? I'm wondering if importing my 1099-B directly will correctly account for everything or if I need to make manual adjustments.

I've been dealing with this exact issue! One thing that really helped me understand what was happening was creating a simple spreadsheet tracking all my MSFT trades with dates and amounts. When I mapped it out chronologically, it became clear where the 30-day overlaps were occurring. What I discovered is that TD Ameritrade's wash sale identification is actually quite accurate, but their 1099-B presentation can be confusing. The key is understanding that when they show a "W" code next to a transaction, they're not saying that specific sale created a wash sale - they're indicating that the loss from that sale is being disallowed because of a replacement purchase. Also, don't forget that if you have any mutual funds or ETFs that hold MSFT as a major position, purchases of those could potentially trigger wash sales too. It's not just direct stock purchases that count as "substantially identical" securities. The good news is that as long as you report exactly what's on your 1099-B, you should be fine tax-wise. The IRS expects you to use the broker's calculations unless you have a specific reason to believe they're wrong.