4 Replies Latest reply: Nov 3, 2009 6:53 AM by Screaming.Pict
Screaming.Pict Level 1 Level 1 (0 points)

I have a particularly weird problem.

In Mail.app I have a Mobile Me account, a personal IMAP account and an Exchange account (working over IMAP etc. as it's Exchange server 2003 so I don't get all the fruity Snow Leopard/Exchange goodness).

The problem I have is this- in the office they block access to external SMTP servers (quite rightly).

If I send a mail through my Mobile Me or personal IMAP account and forget to tell it to use the internal work SMTP server then Mail.app will sit forever trying to connect to the external SMTP server and never time out (or if it does timeout it must be more than a few hours).

This isn't a huge problem in and of itself. However from this point on any mail I send will sit behind the stalled e-mail in the queue and never go out- so even my internal mails hang around not sending.

The only indication of this is the non-stop spinning wheel on the sent items folder and the never-ending 'Connecting to smtp.me.com' in the activity window.

The only way to resolve this is to go to the activity window and cancel all connections to the offending SMTP server. At that point the 'Outbox' folder will appear in my folder list and show me all of the e-mails it hasn't sent. I then have to open each one individually and click send again, at which point they go out (provided they still have the correct internal SMTP server selected).

MacBook Pro 15" 2.33GHz, Mac OS X (10.5)
  • Ernie Stamper Level 8 Level 8 (37,555 points)
    Not sure how to prevent this, although I don't understand why it does simply fail, quickly, and allow you to change the SMTP. If you click on Window and choose Activity, can you then click on the Stop sign beside the sending transaction and then correct?

  • Screaming.Pict Level 1 Level 1 (0 points)

    Thanks for the response. I have previously seen Mail.app fail to send and bring the message back up telling me this- but that usually happens quite some time after trying to send, if at all, and I don't recall ever having this error happen in the office (where they are blocking these ports).

    I have had similar issues when travelling and trying to send through hotel networks that typically block port 25- even then I rarely get a failure message (note that this has been happening both on 10.5.x and my clean install of 10.6.x)

    I did check to see if the network here was doing some spoofing on SMTP ports but it isn't;

    #####:~ #####$ time telnet smtp.me.com 25
    telnet: connect to address Operation timed out
    telnet: Unable to connect to remote host

    real 1m15.019s
    user 0m0.002s
    sys 0m0.003s

    I get the same 1m15s timeout on port 465 & 587, yet Mail.app never seems to give up trying.

    I tried sending to an external SMTP server without SSL to see if the behaviour was any different- but after 15 mins it's still trying so I guess not.

  • Ernie Stamper Level 8 Level 8 (37,555 points)
    You should keep your smtp.me.com set to be presented on Port 587 for best result when traveling. Most every venue blocks using it and similar SMTP on Port 25. Of course your work venue may block every other SMTP.

    Did you get a chance to test whether Activity will let you quickly cancel a Send on the blocked SMTP?

  • Screaming.Pict Level 1 Level 1 (0 points)

    Yes- I can always cancel by clicking the big red 'Stop' button in the activity window (this is what I was describing in my original post as the only way to resolve the issue).