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I am using Google Apps to host my own domain, and uses IMAP to fetch the mail to OS X Mail program.

It is working well in every aspect except one. I can not send emails to myself with OS X Mail. They never return. I'm not getting anything bounced or any error messages.

  • Sending to any other email address works.
  • Sending from my phone works.
  • Sending from my Windows computer works.
  • Sending to myself from another (identically configured, also hosted through google apps) email account within OS X Mail works.

I'm scratching my head, I can't figure out how to troubleshoot this.

I am often sending mail to myself as a way to take notes, but also to put files onto the IMAP-server.

The servers I'm using are and port 993 SSL.

Any help is appreciated.

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up vote 1 down vote accepted

This sounds like a problem I read about on the Risks digest where gmail considers incoming messages duplicates (and hence discards them) if they match messages already in the account, including the accounts's sent mail folder (i.e. the message was sent from the same account). Maybe OS X Mail is putting the outgoing messages in sent messages, but the other methods you tried don't do this?

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You are right, that is part of the problem. I found out that I logged in to my SMTP-server with the other accounts user name (OS X Mail stores the SMTP-server with it's credentials and reuses them if another account selects that server). Changing the SMTP-login fixed it. However, now my emails to the other email address it automatically sent to that email address "sent mail"-box. Funny! However, I don't mind that. – Mattis Oct 6 '11 at 11:08

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