I'm sure this has been covered in this forum, but I couldn't find it searching.
I was having this error:
Connecting........_____
on a couple of boards, a Wemos 8266 R1 D1 and on an RSP WROOM 32 and changing the upload baud rate to a lower setting made it so that I did not have to hold the button.
I found this suggestion on the Random Nerd Tutorials site.
Connecting........_____ fail upload
Connecting........_____ fail upload
Old controls guy, SW Ontario, Canada .
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