Message was edited by: Kappy
I am having a similar issue and tech support wasn't able to resolve on my first call I have items stuck in my outbox but they are either not being sent and just stuck or being sent over and over to the same person. I haven't had issues in the past but for the past few weeks it has been non stop. Tech support said it was because I was on wifi but that doesn't make any sense to me at all.
Since my last software update I have been having this problem as well. I was told to redo the server setting and after several attempts something happened and I was able to send mail. This was about two weeks ago? But yesterday the problem has come back. I think there is a bug in the mail program as it seems to affect my server that is on my own website I have with Netfirms as well
My friend is having the same problems on his 24" iMac.
There IS a workaround, but it is NOT permanent, and he's having other du-plicate/triplicate email problems as well, all after Mac's last update (previous to the big 325 meg one).
With Mail open, go to preferences, then to accounts, then on the outgoing mail server selection box - open it and click on 'Edit SMTP Server List', then select the Shaw mail account, then the advanced box, if custom port is selected click on the one above, or if default port is selected click on custom port, then reclick the button that was previously selected, shut everything down, click save when it asks you, then your outgoing mail will work again, temporarily. It WILL screw up again till Mac stops trying to blame Shaw for the problem - it is a MAC problem, but it is disguising itself to look like it is originating from the server. It is NOT - the Shaw technician had me download Thunderbird email program, and we replicated exactly the same problem - for some reason, OS 10.6.6 is not remember the settings for the ports correctly, and this seems to be the culprit. Time to admit culpability and fix it, Apple! This is really annoying.
Had the same issue.
After finally tracking down someone at SHAW that knew something, we sorted it out. It turns out that Shaw has recently stopped allowing polling of their outbound mail servers.
The fix, set your outbound mail server (shawmail.XX.shawcable.net - where XX is your nearest city) to use a custom port. Set it as PORT 25.
That has done the trick for me and all my clients. Hope it helps you as well.
Cheers from Winnipeg
Still appears to be a problem, Shaw said it was Apple hardware related which is "amazing" to say the least! I have never heard this one before but who knows in this world. I have 2 Macs, one 2010 and one 2012(new) old one no problem, new one problem.
Anyways, setting the custom port to 25 worked like a charm. Closed and opened Mail and still kept the port 25.
Thank you for the fix.