Significant delay in Mail clearing outbox after mail sent

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Level 1

14 points

Significant delay in Mail clearing outbox after mail sent

I have an Apple computer that, when you send email, the messages are getting stuck in the outbox for several minutes before they vanish into the sent items box. The troubling part of this is that the messages are being sent instantly.

My rule outs include a bug with Mail, or maybe the SMTP server isn't returning with a 250 code. With Outlook, I know how to find that successful code, but I'm not sure where to go inside of Mail to see that come in.

Anything else I need to look at? Anybody know how to watch that 250 code come in? I do think I'm going to run wireshark and see what I can determine - but since the mail server uses TLS, I'm not sure I'm going to see the code come back since it will be wrapped in encryption.

Posted on Jul 9, 2014 8:10 AM

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Answer 1

Linc Davis

Level 10

209,739 points

Jul 9, 2014 9:43 AM in response to JessikaElla

Is there a delay when you telnet to the server?

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Answer 2

JessikaElla Author

Level 1

14 points

Jul 9, 2014 12:25 PM in response to Linc Davis

FYI: We're using gmail. I can telnet into the SMTP server without any delay at all. The problem appears to be exclusive to the Mac clients in the office.

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Answer 3

Linc Davis

Level 10

209,739 points

Jul 9, 2014 1:25 PM in response to JessikaElla

Gmail is a deliberately broken implementation of IMAP that often causes problems with Mail. The problem seems to have gotten worse in Mavericks. Google has no incentive to make Gmail work well with any mail client, because the company makes money by delivering targeted ads via the Web. The Gmail servers analyze your messages to gather information about you and your contacts that Google can then sell to marketers, or to anyone who will pay for it. You agreed to those terms when you registered a Gmail address. The marketers—not Gmail users—are Google's customers and the ones it aims to please.

I suggest either not to use Gmail at all, or to access it through the website as Google intends. You might get better results with another email client. I don't recommend any one in particular.

If you insist on trying to make Gmail work with Mail, the following links may help:

Configuring OS X Mail For Gmail Without Duplicates

Setting up Apple Mail to Rock and Roll with Gmail

Apple Mail and Gmail Part Deux

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