12 Replies Latest reply: Jan 8, 2009 8:04 AM by Carmino
Pentigoth Level 1 Level 1
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)
  • dogger73 Level 1 Level 1
    Yup..... same problem here, although it started last night after sending a mass of emails. I didn't change any settings.
  • ArabianDQ Level 1 Level 1
    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.
  • L3photographer Level 1 Level 1
    I am having this problem as well. I am receiving emails, but cannot send any, even to myself. When I have contact me mail customer support in the past on different issues, they have told me there is no problem (when I know there is), so if someone else can figure this out, let us know. Thanks!
  • DavidField Level 1 Level 1
    Me too, was Ok earlier today, I use Mac mail with AOL but it's not a Mac problem as the other computer on my network is a PC running outlook and it won't send mail either. It happened to me once before & I connected onto aol using https://my.screenname.aol.com/_cqr/login/login.psp but this page doesn't seem to exist any longer.
  • DavidField Level 1 Level 1
    Just discovered how to reset AOL mail. Login to AOL mail via web. Try sending an e-mail to anybody, Before it will send another screen will come up asking to type in the characters in an image. Once that's done the e-mail works again. Hope this helps those who have the AOL problem.
  • erinsita576 Level 1 Level 1
    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...
  • Phil Waters Level 1 Level 1
    Not real sure about the instructions here, but I don't get a screen requesting that I type in the characters in an image. All I get after sending is the jumping AOL guy and a message that my mail has been sent.
  • BobKrchnavek Level 1 Level 1
    This web site helped me with the same problem:


    Essentially, you go into System Preferences and change a setting. I use Verizon and it
    just stopped working for me even though I did not change anything. As soon as I
    made the change, the mail went out. Good luck.
  • BDAqua Level 10 Level 10
    Hi Bob, and a warm welcome to the forums!

    Thanks for the tip... indeed a strange cure that is!
  • L3photographer Level 1 Level 1
    I tried the one answer that seemed to help people (the Built in ethernet steps), but I am using Airport for internet connection, so this did not help me. Now that I have paid for this email, it would be great to be able to use it from my Mail app!!
  • Marcelo Lannes Level 1 Level 1

    Try doing this:
    Change the number to 1492 as described above.
    It worked instantaneously for me.

    Good luck!
  • Carmino Level 1 Level 1
    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!