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You may need to check your brokerage to see if they are allowing third-party access. Although the following Help Article is for Schwab, it is possible that your brokerage has restricted TurboTax's access to your statements unless you grant consent. So you might need to do something similar to what is described here How can I fix my 1099 import issue?
I had no broker upload problem. But 2 of the 1099s did not "take" even though they were visible in TT. 1 was recorded after a few repeats. 1099-int needed 19 repeats. I never learned why it failed or succeeded. My several frustrations with TT for 2020 means I will look elsewhere for 2021.
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