Mail keeps asking for account password when trying to send via Yahoo

  • 2020 M1 MBA running Monterey
  • Multiple times a week, Mail.app asks for password when trying to send...
  • ...then chews on the password for several minutes before coming back with the nonsensical error "This account already exists"...
  • ...then 10-15min later, even with that error message still displayed, suddenly we hear the "Woosh!" and the message has been sent
  • ...except once in a while, entering the password works immediately


  • The password it wants is the app-specific password (login password produces an error immediately when entered under these circumstances)
  • Connection Doctor chews and chews and chews on the SMTP connection for about 20 minutes before finally producing a green light
  • We have tried removing Mail.app's app-specific password at mail.yahoo.com and creating a new one — no dice
  • This problem cannot be reproduced on other email apps
  • There is no problem logging into mail.yahoo.com via browser


  • This is only the latest problem we've had with Mail.app and Yahoo
    • Previously we had to switch from IMAP to POP to stop Mail from eating up GB/day of bandwidth by constantly syncing folders over and over and over and over
  • And even though we've disabled the IMAP account, it still appears as one of the options for Outgoing Mail Server in Preferences > Accounts > Server Settings...
    • HOWEVER it's also impossible to get rid of:
    • When we go to Edit SMTP Server List, the IMAP account's STMP is not listed


Would love some knowledgable suggestions.







Posted on Jan 23, 2022 10:18 PM

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5 replies

Jan 24, 2022 12:46 PM in response to 100 Watt Walrus

Try going to utilities- keychain- passwords. In login, system or iCloud. Find any That are Yahoo mail. right click on it -get info -check show password. You'll be prompted for your password. Then if the password is not the one for your Yahoo email account you can delete that keychain. I had this once as I had more than one keychain password for my main mail account.

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Mail keeps asking for account password when trying to send via Yahoo

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