@gmail I'm trying to add another Gmail account in the "send thru your SMTP server" in Gmail, and I'm getting "Authentication failed". The same password and port work sending directly from a script. Everything was working yesterday, and broke today. Help?
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I wonder if it's related to this notification I got in December 2019?
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Replying to @smortimerk @gmail
Yes very likely. The problem was it wouldn't let me add an app specific password even. The problem cleared up later so they clearly made a mistake rolling that out.

May 8, 2020 · 4:38 PM UTC

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Replying to @aaronpk @gmail
I've had such headaches adding app passwords. The fact that it requires you to enable 2FA to add one, and then to disable 2FA before you can use it, without actually telling you that that's what you need to do... I wonder was it made to be confusing on purpose!