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In the United States, it is tedious to keep track of taxable capital gains in a given tax year when taking into account the wash sale rules. Is there any program or web-based service that can make the task easier and possibly help prepare Form 8949? Bonus point if it could import the trade history from typical US brokerage accounts. No preference regarding the license, the cost or the operating system.

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In 2008 and 2009 I traded extremely heavily. Because I scale in and out of positions, I had 100's of wash sales and it was impossible to manually reconcile them. I'm no stranger to math or spreadsheets. Even so, I gave up in frustration because it was a monstrous task. For example, scaling in and out of 20 trades in one stock can turn into 50 trades on the 8949 form. Imagine the precision needed, without error, to prorate these if wash sales are involved and a portion must be carried over to subsequent trades? MENSA 190?

I used a program called Tradelog which handled all of this almost flawlessly. Almost, meaning you have to make a few inputs for situations like stock splits where the number of shares don't match EOY. No biggie. They offered 3 annual subscription levels based on the number of trades made and the highest is allows unlimited trades. I used past tense because there's a new owner and I don't know if anything has changed. I believe that they still offer a 30 day free limited number of trades trial subscription.

Gainskeeper is another investor tax accounting program. I have heard good things about it but I know nothing more than that.

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    Thanks very much good to know! Can they automatically import trade history from the brokerage account?
    – Franck Dernoncourt
    Commented Feb 8, 2021 at 14:36
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    Yes, they can automatically import trade history from your brokerage account but you'd have to check to see if your broker is one that they link with. I found downloading an entire year a little funky if I tried to download in one fell swoop (1000's of trades) but doing a few months at a time ran smoothly. And thanks for providing the SPACs link again.
    – Bob Baerker
    Commented Feb 8, 2021 at 14:44

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