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One morning Mail on my Mac was working perfectly. At noon, I upgraded to Mavericks, then I could not send mails anymore!

I could read my mails but not send them (though I changed nothing in the configuration). I get the message: "authentication failed"!

My SMTP servers (two of these university based) are ok… So either:

  • The new version of Mail is no longer pleased with the server credentials (though I checked these)
  • The new version of Mail sends wrong information (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 app?

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3 Answers 3

Reset to default
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I have had the same problem... Spent two days then found it so simple:

  • Open Mail.app and go to your SMTP account settings;
  • Click on the Advanced tab and change the authentication method to password;
  • Input your mail as username and the password;
  • Voilá! Outgoing mail traffic working!
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  • I followed this, but it was not enough. It already was set to password. What I changed then, was switch to none, back to password, re-enter password, restart mail. And that did it. Even after restarting the machine sending mails on this particular account was working.
    – DisplayName
    Commented Mar 23, 2014 at 18:12
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I am having the identical problem on two of my mail accounts since upgrading to Mavericks this morning. Actually, for months I had this problem intermittently on the previous operating system but it seemed to right itself. I'm guessing Apple must have tweaked something along the line. My advice would be, don't knock yourself out trying to solve it. It's almost certainly nothing you've done. My Incoming mail arrives fine and I also find that the outgoing mail suddenly sends itself after I've almost given up the will to live! I also have an iCloud email address which I use without problems when I'm desperate to send in a hurry. I hope Apple will get onto this as it's completely unacceptable to have the issue again on the much awaited Mavericks.

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Just look if the SSL box is checked. If it is, just uncheck it. It will change the ports automatically.

Try to end the session and reopen Mail.app.

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