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One morning mail on my Mac was working perfectly

At noon I updraded to Mac OS X 10.9 (Mavericks)

Then I could not send mails anymore!

I could read my mails but not send them (though I changed nothing in the configuration) authentification failed!

My SMTP servers (two of these university based) are okay. These are not Gmail things!

So either:

  • The new version of Mail is no longer pleased with the servers credentials (though I checked these).
  • The new version of Mail sends wrong infomrmation (password) - but since these are still here I am wondering if there is some encoding fancy in the protocol that is not working anymore (yes there are accented characters in these informations!)

What I can I do? Can I downgrade and load an earlier version of the Mail tool?

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Not to sound cliché or anything, but did you try logging out and back in or removing that email and trying to add it again? Authentication usually has to do with security and most times relogging will fix that. I've had this happen to me too, hope this helps

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  • Ditto ... I've had a similar issue and nuking the account and recreating it (IMAP based) fixed it.
    – Hogstrom
    Aug 28, 2018 at 15:18
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If the “Show in IMAP” setting under All Mail in your Gmail account is deselected, then any time you move a piece of mail from your inbox in Mac Mail to another folder, that message will be duplicated. The duplication occurs if you switch between different mailboxes or if you close and re-open Mac Mail.

Thankfully, there’s a simple way to fix the issue, though it could take up a significant amount of hard drive space and Internet bandwidth. All you have to do is re-enable the “Show in IMAP” setting for All Mail by logging into your Gmail account, opening Settings, and checking the “Show in IMAP” checkbox for All Mail under System Labels.

http://www.digitaltrends.com/computing/gmail-mac-mail-os-x-mavericks-problems-apple/

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