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I'm trying to drag the file from Finder to TT2020. It worked.

 

Since I go back to 1988 on mac, and the original two-floppy IBM PC, this isn't my first rodeo. That said, "Open TT2019>Close TT2019>Open Finder/Recents>Open TT2020>Close TT2020 but leave it in the Dock>Drag 2019 file to TT2020 in the Dock>Approve Transfer" isn't a user-friendly solution.