issues with sending attachments: macmail or gmail?

Discussion in 'Mac Apps and Mac App Store' started by tim2short, Oct 24, 2007.

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  1. tim2short, Oct 24, 2007

    tim2short macrumors newbie

    Joined:
    Aug 12, 2007
    #1
    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!?
     
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  2. littlevish, Oct 24, 2007

    littlevish macrumors member

    Joined:
    Oct 18, 2007
    #2
    What happens when you try to send one?
     
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  3. tim2short, Oct 24, 2007

    tim2short thread starter macrumors newbie

    Joined:
    Aug 12, 2007
    #3
    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.
     
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  4. mudaudio, Nov 29, 2007

    mudaudio macrumors member

    Joined:
    May 15, 2007
    #4
    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.
     
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  5. mikefedora, Jul 29, 2008

    mikefedora macrumors newbie

    Joined:
    Jul 29, 2008
    #5
    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.
     
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