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I have a weird problem that started just today. I am using Apple Mail on a Leopard machine, connecting to Gmail. Fetching e-mail works just fine. My SMTP settings are also correct. Still, I can't send mail, it will display a pop up saying that "transferring the content to the mail server" failed (translation from German, could be different in English OS X versions).

I have verified the following:

  • My SMTP settings are definitely correct. I have not changed them and the issue appeared today.
  • Also, I went through the Apple online configuration for Gmail accounts and did not have to adjust any setting.
  • I can run network diagnosis and it will connect to both POP and SMTP servers without a problem (all green lights)
  • The Telnet details will show me the HELO message from the Gmail servers, so there's no authentication failure.
  • will not show any messages related to "mail" when I try to send the mail, so there's no specific error message
  • The mail I'm trying to send does not have an attachment, it is plaintext only
  • I can login to and send mails without a problem
  • The recipient address exists and contains no syntax errors
  • I can also not send mails to myself
  • When using another IP and ISP (through VPN), it still doesn't work

As for my settings: I connect to and for advanced settings I choose password-based authentication with user: and my password. I let Apple Mail try the default ports (for SSL and TLS, respectively).

Again: I have not changed a thing between yesterday and today. What is causing that strange behavior? Any help would be much appreciated.

If you have the same issue, please don't answer below. If you have no real answer to the problem, make it a comment on the original question.

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It seems like Google is having some problems today. I can't even log into my Google account without 502: Server Errors. This may be the cause. – squircle Jan 15 '11 at 18:03
Hm that's strange but it could be possible. It surprises me though that I can connect by telnet. – slhck Jan 15 '11 at 18:20
Thanks for the amendment, I will put this into the question, too, if you don't mind. Or maybe let it be migrated to webapps.. – slhck Jan 15 '11 at 21:38
Never mind, at least I am confident this issue will resolve itself. Initially I thought maybe the problem was something different. – slhck Jan 15 '11 at 21:50
+1 for If you have the same issue, please don't answer below. – Nifle Jan 16 '11 at 0:29

From time to time I get errors when sending mail through Gmail's SMTP server. It always solves itself without my intervention. I just need to wait a few minutes/hours.

I would abandon Google's SMTP server were it not for keeping a history of my received/sent mail on Gmail.

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protected by Jeff Atwood Jan 16 '11 at 4:15

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