@torchill
I ceased being a SuperUser when when Intuit switched from SUs to the "Champion" program, so I'm not going to take a deep dive here, but I'll mention a few "top of mind" thoughts.
- The TurboTax 2020 program is completely capable of properly reporting the sales of stock acquired via an ESPP if you enter the sale correctly, a process TurboTax made more tricky a few years back. This isn't a "TurboTax 2020" issue.
- The page that comes up asking about what's been reported on your W-2 comes up as the very last page of the "Stocks, Mutual Funds, Bonds, Other" interview, it doesn't come up when you enter your last security sale. You have to keep going with the interview, hitting "Continue" or whatever until you come to that page.
- Some years back TurboTax changed how that page works. The way it used to work was that TT said "here's the ordinary income we've calculated from your ESPP sales, how much of this is already reported on your W-2?" TurboTax had a box on that page where you could enter that number, (most commonly that number reported on the W-2 would be associated with short term sales only), and if you had compensation associated with long term sales, TurboTax would include the difference on your income tax return as compensation income. That box in no longer on that page. Now, when TurboTax tells you how much compensation it's calculated you can only answer "Yes this is on my W-2" or "No this isn't on my W-2." So if your ESPP sales are both long term and short term and both classes of sales created compensation, neither answer is correct.
This last issue can be circumvented in about 3 different ways and I posted those workarounds many times since TurboTax changed things. I think if you look around in the forum you should be able to find one of those posts and figure this out.
(torchill: I had some problem following your post so maybe posting the details of one problem sale - complete with screenshots - might help somebody grasp the issue in a more tangible way. )
