Infrequently my Mac mail would be rendered incapable of sending email.
It appears the Mac mail client could not connect to the outgoing Gmail SMTP server,
smtp.gmail.com, then after a few hours the connection would be restored automatically.
I assumed that my settings must be fine as they remained constant, it must be a problem on the Gmail servers end, but it was happening too often for that to be plausible.
So I used the connection doctor to see what was happening under the hood.
To access the connection doctor, go to the
Windows->Connection Doctor option in your Mac mail menu.
First thing I noticed was that I was trying to connect to a bunch of different outgoing servers. This is because I had set up separate email accounts (another Gmail and Yahoo mail account). It couldn’t connect to any of them, which was suspicious in itself.
Slash and burn time. I edited my SMTP servers list and I removed the 2 other outgoing servers that I never used, leaving me the one server that I always tried to use.
I ran the connection doctor again and watched the output window.
Failed to connect again, bummer. But I noticed it was using port 25 when trying to connect. That’s not right I thought, it should use port 465 if it’s using SSL. Gmail expects you to use SSL, when connecting and to use port 465.
So I edited the remaining outgoing server connection settings by doing the following.
- Went back to editing SMTP list (described above)
- Clicked on remaining server
- Clicked on Advanced Tab
Instead of choosing ‘Use default posts‘, I specified a custom port 465 and made sure the ‘Use Secure Sockets Layer (SSL)‘ checkbox was checked.
Returned to connection doctor. This time I again failed to connect (boo!) but I got a different error (yay!). Authentication failed. Huh? I didn’t change anything, how did that happen… hmm.
Now I returned to edit the remaining outgoing server. Made sure the Password option was set and I re-entered my account username & password.
Saved settings again.
At this point, I was a little exasperated so I also tried unlocking my Gmail account. I was aware that Gmail lock accounts if they detect unusual behavior, so I made sure my Gmail account was unlocked by going to https://www.google.com/accounts/UnlockCaptcha.
Tried the connection doctor again and sweet baby zeus it connected.
Unfortunately, I cannot say for certain what was the issue. I had tried unlocking the account before I started this and it didn’t connect, so it wasn’t just that.
Anyway, thought I’d post what I tried, might help someone… might also waste 10 minutes of some punter’s life!