I made so many trades last year that I broke
@CharlesSchwab's tax reporting system. This has been such an incredible headache.
YOU CANNOT TRUST YOUR BROKER'S 1099.
Schwab is reporting that I lost $317,000,000 in 2025. As much as I would love that capital loss carry forward for the rest of eternity, I was actually profitable in 2025.
To be clear, I am a small time independent retail trader trading my own capital. These numbers are absurd given the size of my humble trading account.
Schwab is missing thousands upon thousands of my trades, and while they have been working on fixing it for a month, they have been unable to. A dozen different representatives assured me that their tax reporting software was separate from what displays on their web site, and that my 1099 would be correct. NOPE!
You would think the largest brokerage in America would be able to actually, ya know, track your trades. They can't.
I now feel incredibly stupid trusting my broker's 1099's my whole life. I assumed since they have a legal and fiduciary duty to report your tax information correctly, that they would. In reality I have likely been underpaying or overpaying yearly, and I know I am not alone.
If you are a trader, whether amateur or professional, I would highly recommend getting external software that handles taxes and monitoring of your trading activity. (I chose Tradelog). On top of not missing out on thousands of trades, the software can optimize wash sale disallowances in a tax advantaged way. I never would have known to get this software had Schwab not screwed this up so badly.