Entourage through external network stopped working

[jamiebiesemans]

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

This is truly a bizar problem:

After our network admin installed a new domain controller, I could no longer connect to the Exchange-server through Entourage 2008 (or OWA, whatever the browser) when working from home. When connecting to OWA, the browser doesn't return an error page, it just keeps loading without getting to the login screen.

Before this I used Entourage with our Exchange-server (first 2003, later 2007) for years without a hitch.

However, I can connect perfectly if I reboot to Windows through boot camp and with my second pc, which runs Windows.

Strangely, Entourage has no problem connecting when I'm on site at our company.

To make the problem more mysterious, Entourage also has no problem connecting to our Exchange-server when I'm on site at other locations (ie, another company).

Our admin doesn't really have a solution (Macs are officialy not supported). He did suggest the problem might be certificate-based. However, I installed the company certificate into keychain wihtout result. Also, if it was a certificate problem, I don't see how it would be possible that Entourage does connect when I'm off-site at other companies. Btw, I've tried swapping routers, without result.

 

[William Smith [MVP]]

After our network admin installed a new domain controller, I could no
longer connect to the Exchange-server through Entourage 2008 (or OWA,
whatever the browser) when working from home. When connecting to OWA,
the browser doesn't return an error page, it just keeps loading
without getting to the login screen.

Before this I used Entourage with our Exchange-server (first 2003,
later 2007) for years without a hitch.

This sounds like your admin did more than just install a new domain
controller. Did he also change any domain settings such as its name or
did he upgrade Exchange Server too? Did he *replace* an old domain
controller with the new one? Did he change any proxy settings?

A domain controller is by default also a DNS server. Your admin may have
a botched or stale set of DNS records causing problems.

However, I can connect perfectly if I reboot to Windows through boot
camp and with my second pc, which runs Windows.

Not surprising. Windows clients and Windows serves in the same domain
easily share information even in poorly implemented networks.

Strangely, Entourage has no problem connecting when I'm on site at
our company.

Do you connect to your back-end Exchange Server where your account
actually resides or are you using an Outlook Web Access (OWA) address?
While working within the same network I always suggest using a back-end
server address.

To make the problem more mysterious, Entourage also has no problem
connecting to our Exchange-server when I'm on site at other locations
(ie, another company).

Is this really at another company or just another site within your own
company?

Our admin doesn't really have a solution (Macs are officialy not
supported). He did suggest the problem might be certificate-based.
However, I installed the company certificate into keychain wihtout
result. Also, if it was a certificate problem, I don't see how it
would be possible that Entourage does connect when I'm off-site at
other companies. Btw, I've tried swapping routers, without result.

You'd be seeing certificate errors if this were the case.


I have a blog post for ideas about how to optimize Entourage with
Exchange that you might find useful:

"Optimize Entourage to better work with Exchange"
<http://blog.entourage.mvps.org/2008/03/optimize_entourage_to_better_work_with_exchange.html>
or <http://tinyurl.com/56ea7k>

Hope this helps!

--

bill

Entourage Help Page <http://entourage.mvps.org/>
Entourage Help Blog <http://blog.entourage.mvps.org/>
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