issues with sending attachments: macmail or gmail?

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

  1. tim2short macrumors newbie

    Aug 12, 2007
    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!?
  2. littlevish macrumors member

    Oct 18, 2007
  3. tim2short thread starter macrumors newbie

    Aug 12, 2007
    it absolutely will not send in the mail app - after sitting in the outbox for 3-4 minutes. but at, 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.
  4. mudaudio macrumors member

    May 15, 2007
    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.
  5. mikefedora macrumors newbie

    Jul 29, 2008
    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 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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