!cultOfApple
Level 1 (4 points)
Mac OS X

Q: iCloud mail server - Unable To Send With Apple Mail client

OS X 10.10.2

Mail v 8.2

iCloud mail

 

I am still able to receive messages but suddenly unable to send. Messages stay stuck in Outbox.
Screen Shot 2015-03-15 at 1.10.36 PM.png

Mail Connection Doctor reports no problems:
Screen Shot 2015-03-15 at 1.08.11 PM.png

 

If I setup MS Outlook for Mac 2011 with this iCloud account, I am able to send and receive like a champ.

 

Once it starts working, is there a way to change the outgoing mail server to use SSL, i.e., turn SSL to "ON" ?
settings.gif

MacBook Pro with Retina display, OS X Yosemite (10.10.2), 2.8G i7, GeForce GT 750M 2Gb GDDR5

Posted on Mar 15, 2015 10:18 AM

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Q: iCloud mail server - Unable To Send With Apple Mail client

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  • Helpful answers

  • by Linc Davis,

    Linc Davis Linc Davis Mar 15, 2015 11:59 AM in response to !cultOfApple
    Level 10 (207,963 points)
    Applications
    Mar 15, 2015 11:59 AM in response to !cultOfApple

    Please uncheck the box marked Mail in the iCloud preference pane, confirm, and then check it again. Test.

  • by !cultOfApple,

    !cultOfApple !cultOfApple Mar 15, 2015 12:27 PM in response to Linc Davis
    Level 1 (4 points)
    Mac OS X
    Mar 15, 2015 12:27 PM in response to Linc Davis

    Thanks Linc for your suggestion. I went into System Preferences, turned Mail off from iCloud, quit System Preferences and started Mail - there was no mail, as expected since I had turned it off. Then, I quit Mail, went back to System Preferences, turned Mail back on and restarted Mail. All the messages were downloaded back to their respective mailboxes but the message is still languishing in the Outbox...

    settings.gif

     

    Tried sending another message to capture the screenshot of it trying to send:

    Screen Shot 2015-03-15 at 3.20.59 PM.png

    which I think it gives up on without throwing any errors:

    Screen Shot 2015-03-15 at 3.25.25 PM.png

    Just as a note, I have also tried the suggestions at iCloud: Troubleshooting iCloud Mail - Apple Support to no avail... except obviously calling Apple Support (as I don't feel surrendering an arm or a leg for a possibility that Mail might work again, would be too prudent right now).

  • by Linc Davis,

    Linc Davis Linc Davis Mar 15, 2015 12:50 PM in response to !cultOfApple
    Level 10 (207,963 points)
    Applications
    Mar 15, 2015 12:50 PM in response to !cultOfApple

    From the Mail menu bar, select

              Window ▹ Connection Doctor

    Click the Show Detail button. A drawer opens. Try to send a message and post the text that appears.

    Anonymize any private information before posting. That means names, email addresses, contents of messages, and anything else that you don't want to make public.

  • by !cultOfApple,

    !cultOfApple !cultOfApple Mar 15, 2015 1:41 PM in response to Linc Davis
    Level 1 (4 points)
    Mac OS X
    Mar 15, 2015 1:41 PM in response to Linc Davis

    01.png02.png03.png

  • by Linc Davis,

    Linc Davis Linc Davis Mar 15, 2015 1:59 PM in response to !cultOfApple
    Level 10 (207,963 points)
    Applications
    Mar 15, 2015 1:59 PM in response to !cultOfApple

    There's no indication of an attempt to send a message. Did you do that?

  • by !cultOfApple,

    !cultOfApple !cultOfApple Apr 10, 2015 9:58 AM in response to Linc Davis
    Level 1 (4 points)
    Mac OS X
    Apr 10, 2015 9:58 AM in response to Linc Davis

    Yes, I did. It doesn't show up in the logs because, I'm unable to send a message - it goes to the outbox immediately. And this led me to the conclusion below.

     

    And by the way, I did get in touch with Apple Support who went through a number of troubleshooting scripts (including trying to use GMail's mail servers) and ultimately had me reinstall OS X from scratch. None of this worked.

     

    Now this problem of being unable to send mail via my iCloud account, from the Apple Mail client, started only around the end of Feb. What I finally figured was that iCloud mail was using random ports on my machine to invoke its SMTP port. Everytime I would disable the firewall on my router completely, iCloud mail was able to send just fine. Recall that incoming was (and still is) working fine. Anyway, I installed wireshark to ID the ports that were being used when the firewall was down. I set up triggers on my router to open these up, turned on the firewall, but it just isn't working. I will have to play around with wireshark and see if I can figure out what ports need to be opened. Unless you or someone else knows. If I figure it out, I will post it here. Mind you, that I need to figure out not only the source ports that need to access port 587 but also what the real target port is (because I don't think it is just 587 as Apple claims).

     

    By the by, when I asked the Apple Technician (some guy who I was transferred to after 3 other people - the one who asked me to reinstall Yosemite) if there was a way to change the outgoing mail server to use SSL, i.e., turn SSL to "ON", he said no there wasn't and why would one need to secure the traffic to Apple's SMTP server anyway? Seriously?

     

    settings.gif