You are getting those questions because it is an RSU and TurboTax has changed the entry screens. Since you imported the 1099-B, you are showing 2 separate transactions/sales. Had you manually entered the transaction, TurboTax will essentially allow you to enter 'both' transactions/sales in the same entry. The screen you see that on is not for the sale transaction, but only for the vesting details for that lot. This is where your W-2 compensation is calculated from, specifically the Total Shares Vested/Released box.
If you are going to report both sales from the import, separate the vested shares you sold and held (assuming you did not sell all of your shares) from the withheld/traded shares in the Total Shares Vested/Released boxes for each transaction. For the sale of the withheld shares, the Shares Traded for Taxes box will be the same number as the Released box. For the other sale, the Shares Traded for Taxes box will be 0. Be careful to get the totals correct here. This is why David suggested manually entering the transaction instead of editing the import data. 😉
If you manually enter the 1099-B, you don't have to enter the sale of the withheld shares and instead combine the 2 by entering the number of shares withheld for taxes in the Shares Traded for Taxes box on the vesting screen. You would enter the total amount of shares vested (sold, traded and held) on the Total Shares Vested/Released box. In this case, you would only enter the sale of the shares that you received proceeds for (the other sale).
The totals should come out the same, however. But double-check that everything was reported correctly. Make sure the compensation amount calculated in TurboTax matches what was reported on your W-2 (all shares vested in 2019).
The gain or loss (if any) from the withheld/traded shares should be minimal due to timing and/or any selling expense incurred. If sold the same day, there is usually a small loss.
The gain/loss from the other sale (your vested shares sold) should = the difference between the market value per share at vesting and the sale price per share X the number of shares sold.
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