Entourage 2004 cannot retrieve/send mail through a proxy server

[NOSLife]

I have read many posts and messages about using Entourage 2004 through
a proxy. They usually go as follows:

User: "I used Entourage X through a proxy where did the settings go??"

Expert: "Entrourage 2004 uses the Mac OS X network settings for the
proxy. Under System Preferences."

User: "There is no mail (smtp/pop3) proxy listed there!"

Expert: "Just set the web (http/https) proxy and Entourage 2004 will
use that automatically"

User: "It doesn't work!"

[no reply]

Well, I'm here to add a bit more to this problem and ask for an
explanation. I have a user with OS X and Office 2004 11.3.3 (latest
update). They cannot get Entourage to work through our network. I am
the network administrator here and I could not get it to work. The
System Preferences has the proxy set fine. Safari works with it.
Firefox works. iChat works. Entourage 2004 does not work.

I fired up Etherpeek to trace what was going on. I sniffed all traffic
from the user's machine while they ran Entourage 2004 and tried to
check mail...and I found....

Entourage 2004 does NOT use the proxy settings from the System
Preferences Network settings!!!!!! I clearly saw Entrourage trying to
connect DIRECTLY to the DNS name of the mail server defined in its
Accounts....and of course it was refused.

I took down the firewall briefly to troubleshoot. Entourage 2004
worked FINE.

My conclusion: anyone who says Entourage 2004 uses the System
Preferences in Mac OSX to connect through a proxy if it is set is not
correct.

I checked and double-checked the proxy settings. I tested loads of
applications through the proxy, manually defining it AND trying to use
the System Defined proxy. Everything worked fine except Entourage
2004.

If someone could further explain this, I would greatly appreciate it.

 

[Diane Ross]

If someone could further explain this, I would greatly appreciate it.

First, this is not my area of expertise, but I can offer a couple of
suggestions that might get you some help.

1. Rename your subject so that Proxy shows up first. The current subject
gets truncated and some of the exchange gurus might overlook this message.

2. Also ask on the Entourage talk list. This list has many expert users that
do not participate on the newsgroup. You will greatly expand your audience
of people that could help.

How to subscribe to Entourage-Talk:

<http://www.entourage.mvps.org/support_options/subtalk.html>

Hopefully, in the mean time someone will come along to offer some real help.

--
Diane Ross, Microsoft Mac MVP
Entourage Help Page
<http://www.entourage.mvps.org/>
One of the top five MS Entourage resources listed on the Entourage Blog.
<http://blogs.msdn.com/entourage/>

 

[William Smith]

I can't say that I've ever heard of a situation where someone would be
trying to use Entourage behind a proxy server to access an outside mail
server. I'm not sure if this should work or not.

You've left out some pieces of information that would help answer your
question:

1. What kind of proxy server are you using? ISA? Squid? Something else?

2. What method of access are you using on your proxy? SOCKS? HTTP?

3. What kind of authentication is required to pass through your proxy?
If you launch Safari and connect to an Internet site, are you required
to authenticate?

4. What kind of mail connection are you trying to make? POP/SMTP? IMAP?
Hosted Exchange?

bill

 

[NOSLife]

Thanks for replying!

The proxy server is Novell BorderManager 3.8

The proxy as setup in Mac OSX is http/https/ftp (these are the only
options - maybe news, gopher - in Max OSX)

No authentication is needed.....after an initial novell login to the
machine. Safari and other programs all work fine through the proxy.

Trying to make a POP connection to yahoo.

I don't think the problem is necessarily with the proxy itself.
Entourage 2004 does not even attempt to use the proxy set in the Mac
OSX system preferences, Etherpeek shows it attempting to directly
connect to the internet - disregarding the proxy settings in System
Preferences. And in Mac OSX, there is no place to put a pop3/smtp
proxy in system preferences. I've been told it uses the http/https
proxy settings, or is supposed to at least.

Here is one of the replies in this newsgroup about this - lots of
people were using Entourage X through a proxy and want to use 2004
through one:

"Entourage 2004 gets its proxy settings from the OS. Use the Network
options in System Preferences.

Best Regards,

Ryan M. Keith, BSCSE, MCSE
Microsoft Enterprise Messaging Support
Client Server Infrastructure "

Thanks for helping me with this!!!!!!!

 

[William Smith]

Thanks for replying!

The proxy server is Novell BorderManager 3.8

The proxy as setup in Mac OSX is http/https/ftp (these are the only
options - maybe news, gopher - in Max OSX)

No authentication is needed.....after an initial novell login to the
machine. Safari and other programs all work fine through the proxy.

Trying to make a POP connection to yahoo.

Do you possibly have something in your Mac's Bypass proxy settings such
as the name of your email server or its domain that would be keeping the
traffic from trying to use your proxy?

I'm still checking into whether or not Entourage should work through a
proxy.

bill