Resolved Mail not sending messages (Gmail IMAP)

umiwangu

macrumors 6502
Original poster
Sep 4, 2006
478
0
Malawi
I upgraded to Mavericks about a month ago. I had been happily using Gmail with Mail in Mountain Lion. I should have done my research before upgrading, but I didn't, so now I'm learning about the world of hurt that is Gmail + Mail.

I just found out this week that emails I've been sending have not been going out and there is no record of them. Right now I can think of three emails that I wrote to three different recipients that apparently didn't show up in their inbox and don't show up in my Sent Items. This kind of sucks, mainly because I don't know what did and didn't get sent.

I'm on 10.9.1.

Maybe I'll just use Airmail for the time being.
 
Last edited:

satcomer

macrumors 603
Feb 19, 2008
6,346
946
The Finger Lakes Region
Check your Mail's menu item 'Window' and select' Connection Doctor'. In 'Connection Doctor' have it print out the results so joy can see where it's failing to get to the SMTP Gmail server and thus can help you trace down and fix the problem.

Also read the article How to make Mail and Gmail play together nicely. Plus have you deleted you Gmail Mail account, reboot and add it back via System Preference, Internet Accounts pane.
 

umiwangu

macrumors 6502
Original poster
Sep 4, 2006
478
0
Malawi
Check your Mail's menu item 'Window' and select' Connection Doctor'. In 'Connection Doctor' have it print out the results so joy can see where it's failing to get to the SMTP Gmail server and thus can help you trace down and fix the problem.

Also read the article How to make Mail and Gmail play together nicely. Plus have you deleted you Gmail Mail account, reboot and add it back via System Preference, Internet Accounts pane.
I feel like an idiot now. The emails were all stuck in my Outbox. This morning the wireless router went down and Mail told me it couldn't connect to the Gmail SMTP. I have had this issue in the past, where even if an email is stuck in the Outbox, Mail doesn't necessarily show the Outbox folder.

After putting a new temporary password in the SMTP profile (I have two-step auth enabled), the emails all sent. I will look through the article you linked. Thankfully I didn't go so far as deleting my account. I'm using over half of my 15 GBs of storage for Gmail.

Thanks for the help!
 

umiwangu

macrumors 6502
Original poster
Sep 4, 2006
478
0
Malawi
I found this article from TidBITS which was helpful in understanding some of the nuances of Mail in Mavericks. The other article from MacWorld was written before Mavericks was released and some of the info wasn't as relevant.