tacomaman
Level 1 (4 points)

Q: Requesting help solving a "Cannot Send Mail" issue. Sending the message content to the server failed. Running OS X 9.5. Problem seemed to start after the last security upgrade 4-14-2015

I am having mail issues with my 15" (early 2011) MacBook Pro. Processor speed 2 GHz Intel Core i7. Memory has 4 GB 1333 MHz DDR3. Storage capacity 500 GB with 419 available. Running OS 10.9.5. Mail version 7.3.

 

I am getting the pop up box message: Cannot Send Mail - Sending the message content to the server failed. This pops up every time I open my mail. Just started since the last security update of April 14, 2015 Version 1.0. I have not tried anything other than researching what that message means. I don't think I have changed anything that would have caused the problem.

 

Thanks for any help that you can provide that will fix this issue.

 

Chris

MacBook Pro (15-inch Early 2011), OS X Mavericks (10.9.5), null

Posted on Apr 20, 2015 12:46 PM

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tacomaman

Q: Requesting help solving a "Cannot Send Mail" issue. Sending the message content to the server failed. Running OS X 9.5. Problem se ... more

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  • Helpful answers

  • by Linc Davis,

    Linc Davis Linc Davis Apr 20, 2015 4:00 PM in response to tacomaman
    Level 10 (207,936 points)
    Applications
    Apr 20, 2015 4:00 PM in response to tacomaman

    If you can’t send or receive email on your Mac - Apple Support

  • by tacomaman,

    tacomaman tacomaman Apr 20, 2015 4:21 PM in response to Linc Davis
    Level 1 (4 points)
    Apr 20, 2015 4:21 PM in response to Linc Davis

    No problems receiving mail. I have sent and had confirmed receipt of mail. Connection Doctor shows no problem connecting to the servers.

  • by Linc Davis,

    Linc Davis Linc Davis Apr 20, 2015 4:24 PM in response to tacomaman
    Level 10 (207,936 points)
    Applications
    Apr 20, 2015 4:24 PM in response to tacomaman

    From the Mail menu bar, select

              Window ▹ Connection Doctor

    Look for the disused SMTP (outgoing mail) account in the window that opens. Double-click it. Another window will open, showing a list of all the outgoing mail accounts. The unwanted one will be selected. Click the minus-sign button to delete it, then click OK.

    If there's more than one unwanted account, repeat.

  • by tacomaman,

    tacomaman tacomaman Apr 22, 2015 7:26 PM in response to Linc Davis
    Level 1 (4 points)
    Apr 22, 2015 7:26 PM in response to Linc Davis

    I have done as you suggested and selected a disused SMTP account(not sure I had a disused one however) and deleted it. I now have two boxes that pop up that say Cannot Send Mail - this message could not be sent because your account does not have a preferred outgoing mail server. Select from the list below(there is of course, no list below). I went back to Window > Connection Doctor and selected a preferred outgoing mail server(only one account that did not have one selected already) and still keep getting those two boxes that say Cannot Send Mail.

  • by Linc Davis,

    Linc Davis Linc Davis Apr 23, 2015 6:01 PM in response to tacomaman
    Level 10 (207,936 points)
    Applications
    Apr 23, 2015 6:01 PM in response to tacomaman

    I'm not sure I understand your response. Do you have any outgoing mail servers now?

  • by tacomaman,

    tacomaman tacomaman Apr 23, 2015 6:37 PM in response to Linc Davis
    Level 1 (4 points)
    Apr 23, 2015 6:37 PM in response to Linc Davis

    Probably some frustration coming out in my response. Sorry. Actually, the problem cleared itself up this morning. Two e-mails that I sent about one week ago, reappeared when I opened my Apple mail. I simply resent them and the Cannot Send E-mail boxes are gone. Everything is situation normal.

    Thanks for your help!

  • by hedgehog1749,

    hedgehog1749 hedgehog1749 Mar 22, 2016 4:39 PM in response to Linc Davis
    Level 1 (8 points)
    iPhone
    Mar 22, 2016 4:39 PM in response to Linc Davis

    Connection Doctor identified three separate SMTP and IMAP connections for my address.  One took a little bit of time connecting while the other two already had a green light.

     

    I couldn't detect anything astray so closed out.

     

    The message had been sent while I carried out that process, but I don't know if it was coincidental or cause-and-effect.

     

    Thanks N.F. Line .  (NF = Never Fails)