Outlook 2011 with Exchange 2007 and ISA 2006

Posted on 2010-11-18
Last Modified: 2012-08-14
Hi Everyone,

I have a system with the current configuration:

ISA 2006 as an extranal firewall.
Publish Exchange 2007 server with all roles installed on the same box.
Domain Controller

Recently Outlook 2011 for Mac has been released and this works wit hEWS (Exchange Web Services) and does not use the OWA URL for it's configuratio nany more.

I'm struggling to find clear and consise information on how to configure ISA and my Exchange server to work with Outlook 2011.

Internal clients work fine at the moment however externally my clients won't connect. Outlook 2011 gives me no error at all.

Here are the outlook 2011 settings I am using internally which works:

Servname: server01
Use SSL: ticked
Directory Service: (My DC)
Log in with Exchange account: Ticked

This works internally fine.

When I try the following settings externally I get an error in the ISA monitoring saying it can't find

This URL doesnot exist.

I'm at the edge of my knowlege here but it has been mentioned that an external is need for this?

Any help would be great!


Question by:TriumphLTD
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Expert Comment

ID: 34164068
do you have both and point to the external ip address of the ISA server?
Also is your external SAN certificate has all the Subject Alternate Names?

Author Comment

ID: 34164301
The cert does have the autodiscover record but I wlll add the A record to DNS today and let you know tommorow the result.

Thanks for the quick responce.


Author Comment

ID: 34166103
My A record has now populated and I am still getting the same error. I have compared this to a system i have that's exactly the same but works and on that one I don't get the ISA error.

Is there some way I can create on my server as the ISA is saying it can't find it which is correct as it's not there.


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Expert Comment

ID: 34166277
on each CAS server run this cmdlet and post the result:(particularly internal url and external url)
Get-WebServicesVirtualDirectory | fl

Author Comment

ID: 34172147
The internal address is:


The external one is blank which I assume is the issue?


Author Comment

ID: 34186521
Any more thoughts on this? What command do I use to add in this external URL?


Accepted Solution

TriumphLTD earned 0 total points
ID: 34205243
For anyone else looking into this the solution was as folllows:

There was an ISA rule for NTLM on Outlook Anywhere but the Exchange server was set to Basic Auth on the Outlook Anywhere properties.

Author Closing Comment

ID: 34228601
It is the correct solution

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