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Home » GFI User Forums » Kerio Connect » 10.9 Mail.app delay in sending? (Mail.app in Mavericks frequently holds messages in the Outbox and takes numerous minutes to send)
10.9 Mail.app delay in sending? [message #115918] Fri, 05 September 2014 00:15 Go to next message
noamb is currently offline  noamb
Messages: 6
Registered: June 2012
Hey folks,

Under Mac OS X 10.9.x using Apple Mail.app, we've noticed that Mail.app will frequently hold messages in the Outbox, and not actually send them for some minutes. (Maybe up to five?)

We've seen this when sending through different Kerio Connect SMTP servers.

Any thoughts?

Thanks!
noam
Re: 10.9 Mail.app delay in sending? [message #115924 is a reply to message #115918] Fri, 05 September 2014 05:43 Go to previous messageGo to next message
mlee (Kerio)
Messages: 211
Registered: October 2012
Location: Sydney
Have you reviewed the mail log? Have you tried enabling SMTP Client in debug log to troubleshoot? Which version of Kerio Connect are you using? How are the account configured? Integration? IMAP/SMTP? Exchange?

M.


PTSD. BP. OCD. ASPD. BPD. Certified.
Re: 10.9 Mail.app delay in sending? [message #115930 is a reply to message #115924] Fri, 05 September 2014 09:06 Go to previous messageGo to next message
alainrussell is currently offline  alainrussell
Messages: 39
Registered: October 2009
We had this issue as well, tracked it down to using SHA passwords and having the MD5 Auth methods enabled, we disabled these and forced encrypted connections (all our users use SSL so no issue) - fixed all the delays we were seeing.
Re: 10.9 Mail.app delay in sending? [message #116062 is a reply to message #115924] Fri, 12 September 2014 00:43 Go to previous messageGo to next message
noamb is currently offline  noamb
Messages: 6
Registered: June 2012
Thanks for the replies. I've checked into these issues, and here's what I found:

SHA passwords are not in use. MD5 auth is enabled, and I'm asking one user to switch to Password auth instead to test.

I enabled SMTP client and server debugging in Kerio Connect (v8.3.0). The next time the problem was reported, I reviewed the logs. In two separate instances, the logs show that a message was successfully sent TWICE from the Mail.app client (and then successfully forwarded by Kerio Connect to its destination). However, in the minute or two between when these two copies of each message were sent, the message sat in the user's Mail.app Outbox.

We will be updating Kerio Connect to the latest version.

Any other suggestions? This does seem like a Mail.app bug as far as I can tell.

Thanks!
Re: 10.9 Mail.app delay in sending? [message #116094 is a reply to message #116062] Tue, 16 September 2014 00:28 Go to previous message
noamb is currently offline  noamb
Messages: 6
Registered: June 2012
Update: now running Kerio Connect 8.3.1. (8.3.2 is not approved for Kerio Cloud yet.)

Problem seems to have happened again today.
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