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I tried using the free taxaxt software, but seems like it wants me to create a 1099-B for each transaction throughout the year! Is there something wrong here? I thought we needed to fill something called a schedule D.

I've never used taxact, so I'm not sure what it's doing. But a 1099-B is the form on which your broker reports sales proceeds to both you and the IRS - it simply says that StockMeisterVi received $50,000 (or whatever) in proceeds from the sale of stock, funds, etc.

On Schedule D you report all your sales, showing for each of them: what you sold, when you bought it, when you sold it, how much you sold it for, your cost basis, and your net gain/loss. Repeat that for each of your sales (taking care to sort them into short-term and long-term), and if you've done it right, the sum of all your sales proceeds, short-term and long-term, should be the same as what the 1099-B shows. (Or within a few dollars, due to rounding...)

If taxact is indeed asking for 1099-B information, perhaps that's how it learns that you sold stocks or other assets, and after you enter your 1099-B information maybe it will bring up a capital gain worksheet, which will eventually land on Schedule D. (Just guessing here - as noted above, I've never used taxact.)

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