I had exactly the same issue.
TT asks a question that are both poorly worded for anyone who had more than one ESPP purchase period in the year.
I had two ESPP purchases and sales. When entering information for each sale separately, TT asked "Did you buy all this stock at the same time", and I answered "yes" because the stock in that sale was all purchased in one lot. But if you do that, the answers you give will apply to *all* stock sales, not just the sale that you're entering.
The new ESPP workflow is very misleading in a way that is likely to cause people to be double-taxed (or worse) for their ESPP ordinary income, and is worse than 2019 when you simply had to know how to calculate the adjusted cost basis yourself.
