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Was having the same problem as I tried to send more books to my Kindle PW2. Once I added the manual Gmail settings (Have 2FA on so used an app password) and books have started to appear in the cloud again.
Don't have any idea what caused it as Calibre was reporting no errors in sending books but books sent yesterday were not showing up in Google Sent mail but books sent after the fix are showing up in sent mail.
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