I had two different procedures for importing my 1099's with Turbotax Premier.
1. When you try to into import your 1099's via Turbotax are you getting any feedback from the financial site or from Turbotax. I had two situations, Turbotax kept indicating that either my login name or password was wrong, even though they were correct. When I shortened my password to 12 characters, I got no Turbotax error messages and the 1099's were imported. Earlier I got messages that the files simply weren't ready, but they gave an estimated date, which they extended. That was with Wells Fargo Advisors.
2. With Vanguard, Turbotax didn't ask for login name or password, they asked for account number and an account key. That 1099 imported with no problem.
If you are not getting any feedback via Turbotax at the import page, it's really hard to point to whose at fault. Are you really using the 2020 edition? That might be a problem.
