Wednesday, September 3, 2008

Mail Ick

I've been using Mac Mail on a MacBook Pro, and it does the weirdest thing (aka I think this is a bug). Has anyone else seen this?

First let me note that I'm on Leopard. Plugged into the network (wired), Mail is running and works fine. Sending and receiving mail is great.

  1. Unplug from the network (say, go to a meeting)
  2. While unplugged, write a new message and hit send
  • Message shows up in the On My Mac folder repeatedly (about once every 45 seconds)
  • The sending folder shows a spinner for 10 minutes or so
  • An error appears with the message: "The connection to the server "" on port 993 timed out."
This repeats indefinitely, and no other mail can be sent or received, even after the user plugs in. I keep getting that error message once every 2-3 minutes. The only way I can get it to stop is to blow away my Mail preferences file and reconfigure the account.

How frustrating.


  1. Turn off saving drafts on the server. It should get rid of the 45 second problem.


  2. That part worked! Hooray for fewer bouncing icons and error messages.

    Now if only I could figure out the part where it stops sending and receiving when I switch networks...

    Thanks, Adam!

  3. Could it be that "" translates to different addresses when you are on the wired and wireless network? And if that's the case that it keeps trying to connect to the other address after moving networks?

  4. That's actually a really good idea, but at least on the two networks I have available at work, pinging it resolves to the same address.

    I also discovered that on one network port 25 was available for outbound mail, and on both port 465 was available. I've changed that, and it may help.

  5. I've been having serious, ongoing issues with Apple's -- it seems to get worse with every release. I'm not thrilled with Thunderbird though. Let me know if you find a mail client that you find works well.

  6. Even weirder, it's started working again. We had a mail server maintenance period and it's worked ever since. I think I had tracked it down to a problem working with kerberos on the server, but I'm not sure specifically what.

    I don't like Thunderbird, personally. I find it makes my whole system sluggish. Entourage crashed all the time. had occasional issues where I'd have to throw away my prefs and recreate it, but it was pretty rare up until this last incident.