Your Mom Likes My Work

Q: Mac Mail Messages Stuck in Outbox

I have several accounts set up in Mac Mail, some gmail, some others from my website. All outgoing mail is getting stuck in the outbox. I tried the trick of moving com.apple.mail folder and restarting mac mail, but the messages are still stuck.

 

Any ideas?

Macbook Pro

2.5 i7

16gb

OS X 10.10.3

MacBook Pro, OS X Yosemite (10.10.3), 17"

Posted on Jun 2, 2015 7:16 AM

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Q: Mac Mail Messages Stuck in Outbox

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  • by Linc Davis,

    Linc Davis Linc Davis Jun 2, 2015 8:04 AM in response to Your Mom Likes My Work
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    Jun 2, 2015 8:04 AM in response to Your Mom Likes My Work
  • by Your Mom Likes My Work,

    Your Mom Likes My Work Your Mom Likes My Work Jun 2, 2015 8:35 AM in response to Linc Davis
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    Jun 2, 2015 8:35 AM in response to Linc Davis

    Good article, but the connection doctor seemed to be the only pathway to resolving the problem. I ran it and got green light on all but one account. I'm not sure how that one account could cause this issue for all accounts. Something else that's happening is that there are unread numbers next to VIP names even though all emails are "read." I'm not sure if that is related.

  • by Linc Davis,

    Linc Davis Linc Davis Jun 2, 2015 8:39 AM in response to Your Mom Likes My Work
    Level 10 (208,037 points)
    Applications
    Jun 2, 2015 8:39 AM in response to Your Mom Likes My Work

    From the Mail menu bar, select

              Window Connection Doctor

    Click the Show Detail button. A drawer opens. Try to send a test 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 Your Mom Likes My Work,

    Your Mom Likes My Work Your Mom Likes My Work Jun 2, 2015 8:44 AM in response to Linc Davis
    Level 1 (0 points)
    Jun 2, 2015 8:44 AM in response to Linc Davis

    I just sent a test message to myself and it went through just fine. Weird. There's still messages to other people stuck in my outbox. I've also tried changing the "from" email account.

     

    Since it went through, is posting the log info still pertinent?

  • by Linc Davis,

    Linc Davis Linc Davis Jun 2, 2015 9:03 AM in response to Your Mom Likes My Work
    Level 10 (208,037 points)
    Applications
    Jun 2, 2015 9:03 AM in response to Your Mom Likes My Work

    Try sending one of the stuck messages again.

  • by jchrisl,

    jchrisl jchrisl Jun 2, 2015 10:48 PM in response to Linc Davis
    Level 1 (0 points)
    Jun 2, 2015 10:48 PM in response to Linc Davis

    You said all accounts but one were green and wondered how one failed account in Connection Doctor could block the rest. If that one account is designated as the sole SMTP server of choice (the only way mail can get sent), then nothing using that "avenue" will work.

     

    Change the the sending email address to one of your other email addresses, and trying sending again. That can narrow down the problem account.

     

    As for testing by sending a self email. . .

    I've always been told that sending an email to oneself at the same address (or even the same domain) may not be an adequate test. You should send it to a different domain. In other words, if you're testing the sending functionality of a gmail.com email account, send it to an address with a different domain, such as a me.com or hotmail.com.

     

    Personally when I'm having these kind of problems, I simply delete the account in question in Apple Mail preferences or in the system preferences. Then restart the Mac and add that account back using the Add Account wizard in Apple Mail or system preferences. SAVE A COPY of the stuck email before deleting the account or at least copy / paste them to a text edit document.

     

    Another tip: Test your account credentials by going directly to that email's website. For example, Gmail go to Gmail.com, and use your account credentials to login, thus confirming your username and password are correct. If they won't login there, they're certainly not going to login in Apple Mail.

     

    Good luck.