Gmail messages stuck in Outbox in Apple Mail in Yosemite

mail

Today I discovered a whole pile of messages in my “On my Mac: Outbox”  and no matter what I tried I couldn’t get them to send.   I use gmail as my mail server.  The emails looked like they were sending – there was no error message – but they didn’t actually send. They were still in the outbox.  When people started to complain about my slow email replies, I looked and discovered all the emails over the past three days were just sitting there in my outbox!

I checked out the Apple help page here and tried what they suggested. According to the Apple mail connection doctor everything was working fine –   I got all green ticks!

green

I did a Google search and on different forums found all sorts of  ideas:

  • playing round with preference files
  • rebuilding the mailbox
  • typing in my Gmail SMTP server password again
  • changing the Gmail SMTP port settings
  • restarting mail
  • restarting my computer
  • repairing permissions
  • move mail sandbox folders
  • turn off SSL

None of these solutions worked!

Warning: Do not try moving them to ‘gmail outbox’. They will be permanently deleted. (I thought that if I move them to Gmail outbox then they might send –  unfortunately they just disappeared!)

In the end I found this forum from 2012 where someone was suggesting changing DNS settings. This is a very strange because Safari is working fine which means my DNS  is working fine.  I can even receive emails!  Even namebench was working fine.

But sure enough I changed my DNS settings and the problem fixed itself!  This problem has been round since 2012! And the solution still works!

Here’s how to do it:

Go to the advanced tab of the network control panel in system preferences and  click on DNS.  You will probably have the DNS settings for whichever Internet provider  you use.

I put in the google DNS numbers 8.8.8.8

Putting the Google DNS number into my network preferences.
Putting the Google DNS number into my network preferences.

I restarted mail and the problem was fixed.

I didn’t want to use the Google DNS, so I went back and put in my original DNS settings – the problem reappeared!

So for some reason, at the moment,  Apple mail is only sending messages through Gmail if I use the Google DNS server. I am seeing this as a temporary fix, not a solution. I don’t understand why this works at all.

 

 

Posted

, ,

Related posts:


  1. How to get Gmail to send mail in OSX 10.9 Mavericks So it turns out there can be a glitch with Mavericks and Gmail. When I installed Mavericks on my Macbook Pro,  all my messages piled up into my outbox, but weren’t sent. It turned out that Mail wasn’t picking up…

  2. Apple mail changing my ‘From:’ sender account Over the past couple of months our family has discovered a strange little problem. Our emails have been getting mixed up! My daughters have been sending emails, but the replies have been coming to me. I have been sending emails,…

  3. Apple Mail can’t find my Gmail messages If your Gmail messages stop appearing in Apple Mail, or you can’t send emails, or you are getting an error message, here are some tricks to try….

  4. How to change the default OS X email Application. I’m not sure why – I must’ve changed a setting somewhere – but recently whenever I click ‘send an email’ in OS X it opens up a Chrome browser window and tries to send a new email through Gmail. I…

  5. Google Inbox iOS app – a great alternative to Apple Mail App Google Inbox has become my preferred email app for my iPhone. I have been using it alongside Apple Mail for about a year but in the last couple of months I have completely ditched the Apple Mail app in favour…

  6. How to open a browser window that’s logged into a specified Google account I have four different Google accounts and quite often I find myself in a browser in the wrong account. For example I might be trying to edit my church calendar, which resides in my work Google account, but because I…

New Posts

Latest Comments

  2. One Last question, how did you filter your overdue smart list. I have been using relative range past year but…

Article Categories

Comments

14 responses to “Gmail messages stuck in Outbox in Apple Mail in Yosemite”

  1. b

    Thanks, that actually helped!
    After a yosemite update I had to remove the google DNS (i was using before) and now i can send messages again through smtp.. It ist truly the opposite like in your case..

    Reply
  2. RKruger

    I followed the instructions and now I can send my mail. Thanks!

    Reply
    1. Wayne

      Good to hear it worked. This was a strange problem!

      Reply
  3. Viknes

    Excellent fix.
    Cheers.

    Reply
  4. stuck in outbox

    Thank you! I’ve searched high and low, spent a couple of hours at different times and no success. Now I’ve tried your DNS changing method and it seems to be working!

    Reply
  5. tricia

    still didn’t work for me.
    not sure what to do

    Reply
    1. David

      I’m stuck too…did you ever figure it out? What worked?

      Reply
      1. Michael

        Also stuck :/ Any ideas?

      2. Wayne

        Also try quitting mail then re-starting mail. Also try re-starting your computer.

  6. Wayne

    So have you (Tricia, David and Michael) tried every solution in all those links above and none of them have worked? Or did you just try my solution. I am not expecting my solution will fix every case, but it is something else to try if you have exhausted all the other options!

    That is try this:
    https://support.apple.com/en-au/HT204075

    Then these:
    rebuilding the mailbox
    typing in Gmail SMTP server password again
    changing the Gmail SMTP port settings
    restarting mail
    restarting computer
    repairing permissions
    move mail sandbox folders
    turn off SSL

    Reply
  7. Phil. C

    Worked for me also I’m on Mojave,it seems to me it’s an age old network issue of the cloud becoming jammed up over outdated servers, if this fix has been around since 2012 and the problem is still occurring then its shameful

    Reply
  8. Kris

    I have the same problem and now it is 2021, but with a little difference. I have two gmail accounts and one of them works ok in Mail, the other is not. How strange is that. I did not have this issue before. I don’t know why it appeared now. My solution for now is that I move emails to drafts folder and send them out in gmail app on my phone.
    Any ideas?

    Reply
  9. Simon

    I’m on last iteration of macOS that works on my iMac – Catalina – and this cropped up after updating to Safari 15.1: iPhone on ios15 and MacBook running macOS Big Sur unaffected.
    Probably unrelated to the Safari update but Gmail just stopped working soon after, fine on webmail though.
    After trying tons of complex fiddling I gave up and just deleted Gmail account, restarted and re-added from mail > accounts.
    Two minutes later all good, all folders/mails downloaded, just another mac mystery to remain unsolved I guess.

    Reply
  10. Peter Hartnall

    I tried the suggestion re changing DNS to 8.8.8.8. I was sceptical
    but it works beautifully! No idea why but I don’t care! It works and that is all that I need. So thanks for that suggestion. By the way I am using a 24″ iMac with Monterey, and the solution worked OK (but curious because I have a much older iMac 21.5″ that has never had this problem and still receives and sends all my emails ok without me doing anything to the DNS)

    Reply

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.