Thanks for the info. I wish it would have helped, but it didn't for my specific case. Note: I am not an expert; however, I have been using turbo tax and the ESPP feature for >10 years and understand the tax implications for short term very well, not as much for long term, but know enough to understand something seem fishy...
After more playing around I think there is an issue with the windows version of turbo tax. Here is why:
The cost basis used has NOTHING to do with what I put into the ESPP template. It ONLY uses what I am FORCED to put into the first page Before I state it is an ESPP sale. Now that is fine for the stuff that is short term as the ordinary income (that gets me to the cost basis) is reported in my W2. So as long as that is correct (it is.) everything works OK; however, I do NOT get (as I did in past years) the check of how much income should have been reported in my W2 (so still think something is wrong...) So the gain (logged as short term capital gain) is the amount over the cost basis. Again correct for short term sales.
Also, when I enter in a second sale of ESPP ALL the information from the first vest is already IN the ESPP area. So I believe there is an error in how things are being used. In past years I could enter ZERO in the cost basis (or skip entering it) and the ESPP forms would automatically update the cost basis based of what I put in for the vesting information ( this is NOT happening this year.) Also when I complete, even though I clearly state it is an ESPP sale in the questions it states it is NOT a company sale (i.e. not an ESPP sale!!!)
The issue is the long term sales also use that COST basis from the first page (which I DO NOT HAVE) and even if I did it would push ALL of the gain into LONG term capital gains. I know that this is NOT right as some of the gain should be included in the Ordinary income. But since the ESPP forms are NOT changing anything and I don't have a cost basis, it is impossible to get the right outcome. I had the same situation last year and I input the same sale into my 2019 Turbo tax and I get a different result on tax implications!!!! So for sure something is different and wrong and since it is putting ALL gain in the long term into capital gains it makes me think that the 2020 turbo tax has an issue for ESPP. Note I see similar issues on RSUs, but haven't played around enough for that.
