Entourage receiving, but not sending email for one account

[JeighLG]

Version: 2008
Operating System: Mac OS X 10.5 (Leopard)
Processor: Intel
Email Client: pop

I have been using Entourage for a year now interfacing seamlessly and successfully with 3 POP accounts. Yesterday, I noticed that emails being sent via my company account are not being sent. The Send/Receive retrieves emails from all accounts, but hangs up when accessing the company email server. Thinking it was a caching problem, I'd shut down Entourage and restart and the messages would go through...but even that is not working now. I've checked the originating account and that is clean as a whistle. My email item count for that account is less than 800. What's going on and can you help me?

 

[Diane Ross]

I have been using Entourage for a year now interfacing seamlessly and
successfully with 3 POP accounts. Yesterday, I noticed that emails being sent
via my company account are not being sent. The Send/Receive retrieves emails
from all accounts, but hangs up when accessing the company email server.
Thinking it was a caching problem, I'd shut down Entourage and restart and the
messages would go through...but even that is not working now. I've checked the
originating account and that is clean as a whistle. My email item count for
that account is less than 800. What's going on and can you help me?

Is this a POP account connected to your company's server?

1. If you can receive but not send then you have a bad SMTP configuration
2. If you can send but not receive you have a bad POP or IMAP configuration

I would check the "Outbox." It could be a stuck message blocking further
messages from sending.

--
Diane Ross, Microsoft Mac MVP
Entourage Help Page <http://www.entourage.mvps.org/>
Entourage Help Blog <http://blog.entourage.mvps.org/>
YouTalk <http://tinyurl.com/bzcrjy> <-- Entourage mailing list
Twitter: follow <http://twitter.com/entouragehelp>

 

[JeighLG]

The POP account IS connected to the company's server.
The Outbox has no messages in it. I deleted the unsent messages and restarted Entourage. Still no change. I checked out on the webmail account and there are no messages "stuck" there, either.
The SMTP configuration has not changed that I'm aware of. How would one check to see if it's "bad"?
In addition, I deleted, then re-added the account. The next batch of mail got sent, but the following batch did not send. I quit, then restarted Entourage, and the latest batch kicked free, but I think nothing's been solved. Other suggestions?

 

[Diane Ross]

The SMTP configuration has not changed that I'm aware of. How would one check
to see if it's "bad"?

Since your other accounts are still working on your company's server it
doesn't see likely that there was a server update that requires changes to
your SMTP setting, but if there are multiple servers it could be a roll out
issue. We get many reports of non-notification of required updates for SMTP.

You used to be able to use tcpflow, but it appears to be broken under
Leopard. To monitor your network traffic see if one of these can help.

Interarchy
<http://nolobe.com/interarchy/>

Another application I ran into recently that do is EavesDrop....Let it
capture some stuff then double-click any of the lines of text in the main
window to see more detail.

<http://www.baurhome.net/software/eavesdrop/index.html>

At the bottom of this page for tcpflow, you can see what traffic looks like
between Entourage and your server.

<http://www.entourage.mvps.org/troubleshoot/tcpflow.html>

To eliminate a lot of problems, you can try this test for the problem
account only.

1) Go to System Preferences --> Create a New User in Accounts. Switch to the
New User by logging out/in or use Fast User Switching.

2) Open Entourage and enter the problem account. Be sure to set it to leave
mail on server for this test.

3) If it fails in this new user, this eliminates your database and your User
preferences. If it works, then you need further testing in your User's
account to find out what's the problem.

A) To eliminate your Preferences, drag the Identity folder to Shared, then
switch back to your new test User and drag (it actually copies) the Identity
to the Microsoft User Data folder. It will overwrite if they are both named
the same. I would rename the test Identity in case you need it until you get
this problem solved. If the Identity works in the new User then you know
it's preferences in your User's folder.

Be sure to drag back from Shared when you are back in your regular User or
Entourage will create a new blank one.

--
Diane Ross, Microsoft Mac MVP
Entourage Help Page <http://www.entourage.mvps.org/>
Entourage Help Blog <http://blog.entourage.mvps.org/>
YouTalk <http://tinyurl.com/bzcrjy> <-- Entourage mailing list
Twitter: follow <http://twitter.com/entouragehelp>

 

[JeighLG]

It turns out that the mail server did undergo some updates which not only disturbed my Entourage, but Outlook as well.
Thanks for your rapid and very helpful responses.