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Mail: 'Sending the message content to the server failed'

My wife has a MacBook Pro and I have an iMac, both using Tiger and both using Mac Mail with Gmail accounts. We frequently get errors when sending mail - mail cannot send so it puts the messege indefinately in my Outbox. We both recieve mail just fine.

The exact error is:

'This message could not be delivered and will remain in your Outbox until it can be delivered.

Sending the message content to the server failed.'

I tried changing my port 25 to 587 and it did not seem to work. Any ideas?

Thank you.

iMac, Mac OS X (10.5.4)

Posted on Oct 19, 2008 7:29 AM

Reply
12 replies

Oct 31, 2008 10:13 PM in response to dogger73

Did any one ever solve this issue? I sent a few e-mails this evening as usual then this I started getting this message. I made no changes to anything in mail. I can send mail to myself but not to any one else. Connect Doctor indicates no problems connecting to the server. I did try the Windows solution by restarting the computer (which I've never had to do with a Mac!) of course it did not help. I have an AOL mail account and I can go to it through the AOL program and send mail just fine. But Mail is so much faster than AOL I'd like not to have to go back there.

Nov 30, 2008 3:45 PM in response to Pentigoth

I signed my girlfriend up for MobileMe last night, and can't get her computer to send mail. At first I thought that it was a hardware problem, as her machine is reaching "dinosaur" status, but after reading some of these posts I see that people with intel macs are having the same issue...

Anyone have a clue what's going on? I've changed the port from 25, still nothing. Getting frustrated...

Jan 8, 2009 8:04 AM in response to Pentigoth

hi - i posted this in another thread but meant to post it here - oops - i've been following this thread and others for days now - i also have been having safari/email 'sending message content to server failed'/flash 10 plugin problems since latest security/java/qt software update - here's what i recommend and what i'll be doing from now on - before i install any updates via software update i'll be saving the download/installers to a folder as suggested in another topic thread - next i'll be disconnecting my router - and connecting the modem directly to the computer - bypassing the router - once i'm sure configurations/internet/mail are functioning correctly i'll connect the router - all this time my problems were with my router port settings - not safari or flash 10 plugin or mail app - go figure - hope this helps - peace!

Mail: 'Sending the message content to the server failed'

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