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I used to use the "send mail as" feature so I could use the gmail interface for my work emails instead of outlook. My workplace has now mandated 2-factor authentication for their single-sign on, so when I go to add my password in the SMTP configuration, I get an Authentication Failed error because I don't have the opportunity to add the second factor. Is there a way to get around this?

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  • Any updates on this topic?
    – C.Colden
    May 27, 2020 at 16:46
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    unfortunately not. I haven't done much further investigation since posting this. A colleague did some digging more recently but wasn't able to find anything either. May 28, 2020 at 17:22
  • Same results from my side - thanks for the update.
    – C.Colden
    May 29, 2020 at 19:08

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Question is a bit old, but I believe the answer is you need to create an App Password for the account you want to use as an alias. E.g. you have two email accounts a@gmail.com and b@gmail.com. b@gmail.com has two-factor authentication. You want to be able to send emails from a@gmail.com as b@gmail.com. Set up an App Password for b@gmail.com using these instructions. Then when you're asked for a password for b@gmail.com in the "Send mail as" dialog box, use this app password.

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  • worked for me..
    – derelict
    Aug 17, 2021 at 16:51

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