issues with sending attachments: macmail or gmail?

[tim2short]

I've been using my Gmail account in MacMail for a long time now and it has been wonderful. However, the last couple days, I have been unable to send attachments. Things were working great, then randomly it would randomly get stuck on attachments. Even on Gmail's web-based e-mail I have been having issues.

error message:
"This message could not be delivered and will remain in your Outbox until it can be delivered.

Sending the message content to the server failed."

This sucks! Any ideas!?

 

[littlevish]

What happens when you try to send one?

 

[tim2short]

it absolutely will not send in the mail app - after sitting in the outbox for 3-4 minutes. but at gmail.com, it will eventually send - longer than normal. as far as I know, nothing as changed. the nature of the attachment is still the same - no more than 10 MB, jpgs, pdf's.

 

[mudaudio]

Not sure if you found a solution... And I'm not sure if this is pure coincidence, or a genuine solution.

But, last night I couldn't send a zip file of around 600k. Was driving me mad, though I ended up sending through the web gmail.

Tonight I checked my keychain, and noticed a few additional entries for my smtp for gmail. They were duplicates for my gmail account, but ones where I'd forgotten to set the 587 port thing.

i deleted them and now I can send the attachment.

As I say could be conincidence, but it's working fine now, so maybe the additional keychain items were causing a fuss somehow.

 

[mikefedora]

mudaudio, you're my hero!
this problem had been driving me crazy for 2 days. i made sure the gmail smtp port was set to 587 in Mail, closed Mail, then deleted all the smtp.gmail.com entries in the keyring. i restarted Mail, it asked me for the password, and ... success! the attachment that had been sitting in my outbox tormenting me for 2 days is gone.