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Problems connecting to Exchange 2007 using Entourage 2008

Posted on 2008-10-28
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Last Modified: 2012-06-21
My company migrated to Exchange 2007 a little over two years ago.  We have a pretty vanilla install -- aside from configuring a separate Outlook Web Access (OWA) server, we left everything as the default settings.

I recently installed and patched Entourage 2008 on one of our Macs (OSX 15.5, I believe), and am trying to connect to an account.  However, to date I've been unsuccessful, and there's no clear reason what's going wrong.  Is there something I need to do on Exchange 2007 to enable me to connect via Entourage 2008?
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Question by:deathtospam
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by:Darksied9
ID: 22822351
You are pointing the Entourage to the OWA server with Https, and you have made sure that the 128Bit security is enabled on the FrontEnd and Backend Exchange servers?
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by:Darksied9
ID: 22822358
BTW, 128Bit for the IIS for Exchange....sorry.
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by:deathtospam
ID: 22822462
Yes, I have an account set up that points to OWA via https:// URL, and confirmed that it works by pasting it into a Safari tab.

Fairly sure 128bit security is enabled in Exchange, but not 100% certain.  Do you know where I'd look to confirm that?
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by:deathtospam
ID: 22822564
Woops, just saw your comment about 128bit being in IIS.

Yes, 128bit is enabled/required for SSL on the OWA server.  The WWW service is disabled on our Exchange server.
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by:Darksied9
ID: 22822603
Yes.

Computer Manager | IIS Manager, Find the Website for Exchange and choose properties and the setting is on the security Tab I believe...

Also, try pointing the Entourage directly at the Mailbox server...
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by:Darksied9
ID: 22822649
Can the user login to OWA?
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by:deathtospam
ID: 22822667
I've already tried pointing Entourage directly at the Mailbox server (via computer name), but then I get "cannot verify" errors when trying to reach the LDAP and/or Exchange server.  We tried out the HTTPS URL instead and had more success, and the "(Not Connection)" message disappears after we create the account.  However, no mail of any kind is pulled from the server thereafter.

The Mac only needs to be on the same network, right?  It isn't part of the domain right now...
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Darksied9 earned 500 total points
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by:Darksied9
ID: 22822712
Should be fine being on different networks, and not on the domain.  Is it seeing the certificate for SSL as valid?  Is the certificate expired?
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by:deathtospam
ID: 22822724
Interesting... I'll forward that EE item to my boss, since he knows more about OSX than I do, and we'll follow the steps in the answer.
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by:Darksied9
ID: 22839439
No problem, how is it working now?
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by:deathtospam
ID: 22905132
Haven't had a chance to spend enough time trying the stuff out in that other EE answer you linked me to.  Gonna close the question for now (and will assign all points to you) -- once we get started on this again, I'll open up another question.  Tx for the help!
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