Entourage not working with Exchange 2007 on Server 2008

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I have 2 problems while migrating from a Vpop server to Microsoft Exchange.

The first problem i hope is a simple one.

Because we have around 80 clients moving the company from vpop to exchange isn't going to happen over one night which needs to happen for internal emails to work and internal mailing lists. e.g. if i move myself to exchange and send a email to a user who is still working from the vpop server as the email is from the same domain it wont leave the building and sit in their new exchange mailbox which they have not been setup on yet. as we own several domains i've set the exchange server up to use the least used domain and set that as the reply address and the old vpop server uses all the new domains until we move over which does works. i have also setup lan forwarding on the old vpop user for users have moved across to forward emails to the exchange server which also works but.... it is taken about 20min from the point i hit send to the point the recipitent recieves the email. Which isn't really going to work for us. Ideally what i could do is get exchange to relay all mail straight to the vpop server which will send the mail which will then mean the users with vpop will work internally from exchange and also the mailing lists will work.

Right that was the easy one

Now for the difficult one.

First some background.

We are setting up Exchange for the first time on a new server, the server is running Server 2008 and the version of Exchange is 2007 with SP1. We have two servers handling exchange one is the mail hub and the other is for the mailboxes. We also have another server which handles Active Directory which is Server 2003.

Outlook 2007 worked a treat but Entourage on the mac will not work. at first it appeared to be a authentication problem, bad user name and password but we have now got to a point entourage will connect with no errors but it does not recieve any mail or the folder system e.g. inbox, sent items etc. We have been doing some googling and people are having problems which are similar but there are not many people running on server 2008 as of yet. we have tried installing webdav which was suggested, i have tried all the combinations under the sun for the server address with username@domain at the end etc. and we have completely run out of ideas and things to try. Owa is working with no issues which we believe Entourage uses.

Thanks for your help,



Sorry forgot to mention the version of Entourage we are running is 2008 but we have also tried it on 2004 with the exact the same issues and also the same thing when trying with mail on the mac. It seems to be a exchange or server related problem rather than the client.


fixed the first issue but still can't get entourage to work with exhchange.

Any help??


Clarify: Entourage can't receive mail from E2k7, but Outlook can work well

Collect unclearly info:

1. Can entourage send mail?

2. Affected user scope: all entourage users?

3. Where is your CAS server role? Installed in same server with HUB role?

4. Which type of the mail account does entourage use?


1. Go to your event viewer, check if there's any error info in application log (both server and client OS)

2. How many an amount of mails has your entourage client user already had before come to exchange? (in the inbox)

Notes: large amount of mails stayed in the inbox will cause entourage un-receivable


<I'm not receiving e-mail or items in my Exchange account>



A few things you might want to check too:

- Did you install Exchange with the so called legacy support, i.e. public folder database and so on? The fastest way to verify this is the check if there's /exchange/ virtual directory on your CAS server.

- Entourage 2008 SP1 and Exchange 2007 SP1 works in our environment with simply server.domain.com as the server address. Compared to the previous suggestions like https://server.domain.com/exchange/user@domain.com or some such.


KarriR wrote:

A few things you might want to check too:

- Did you install Exchange with the so called legacy support, i.e. public folder database and so on? The fastest way to verify this is the check if there's /exchange/ virtual directory on your CAS server.

- Entourage 2008 SP1 and Exchange 2007 SP1 works in our environment with simply server.domain.com as the server address. Compared to the previous suggestions like https://server.domain.com/exchange/user@domain.com or some such.

Right, actually it used to work in my envirornment as well, Server 2008, Exchange 2007 SP1 Leopard 10.5.3 and Entourage 2008. UNTIL. I installed (stupid, I know) Ms. Configuration Manager 2007 on the Exchange server running both Mailbox and CAS.

This package needed webdav, so I installed the new 64 bit webdav for IIS7, and since then Entourage stopped working. De-installed MS configuration manager + webdav, re-installed the CAS role, re-created the legacy virtual directories (exchange exadmin and Exchweb) even tried to put them under a newly created website. What happens is this, in entourage (be it with auto config or manual) the user can connect, but nothing will be downloaded, when trying to go directly into the browser using https://server.domain/exchange/user@domain.com I get:

TTP Error 500.0 - Internal Server Error

The page cannot be displayed because an internal server error has occurred.

Module IsapiModule

Notification ExecuteRequestHandler

Handler AboMapperCustom-81598

Error Code 0x80004005

Requested URL https://localhost:443/Exchange

Physical Path \\.\BackOfficeStorage\mydomain.nl\MBX

Logon Method Negotiate

That particalar isapi module is davex.dll.

In the even log the following is recorded:

DAVEX to be shutdown. Version

It seems that this DLL is not able to run anymore on the webserver, on a working Server 2008 whenever you go to the above URL, you are re-directed to owa. Whenever I try to connect using Entourage I get the same event id in the event viewer (id is 101 by the way), when using Entourage on the working configuration, mail and folders are downloaded, and the event 101 isn't in the event.

I surely hope someone might have an answer, as I googled for hours and not found anything. Also I tried to install a different CAS, then it only downloads a junk mail folder, and the same ID is recorded on the source mailbox / cas server (not on the " workaround CAS server).


Were you able to resolve this? I've got a similar problem...Server 2008, Exchange Server 2007 and Entourage 2008. It looks like we've been able to get Entourage to connect to the server, but it doesn't sync correctly. No folders, no messages, but no error of a non-connect either.

Suggestions, comments?

Robert Lightner

I am also having the same problem with my Entourage 2008 clients as well. I did notice that the Entourage 2008 clients that can connect and get their folders synced are coming across in the CAS IIS logs as /exchange/alias@domain.com. Whereas my account request is logged as /exchange/alias without the domain name. I'm trying to determine if this is a client issue or serverside. I don't understand why some Entourage 2008 users are able to sync and others can not.

The other thing worth noting is that the " physical path" associated with the virtual directory /exchange on the CAS server and Mailbox server. My install took my forest root domain name and plugged it into all of the physical paths for all virtual directories even though I am not using that domain name as my default accepted domain. Here's what my physical paths looks like. \\.\BackOfficeStorage\forestroot.com\MBX

If anybody has some insight on to solve this problem I would greatly appreciate your post.


Hi There,

I have exactly the same problem, with Entourage 2008 connecting to Exchange 2007 CCR SP1 running on Windows server 2008 x64.

IMAP work just fine but using exchange method will fail. Entourage will connect but no folders will show on the client.

Like the application will not know how to transylate the view to show it???

I guess it is IIS webdev legacy related issue.

Anyway, do you guys know, if I will make the call to Microsoft and pay the $ , are they will be able to resolve it? did anybody made the call already?



Todd Hawkins


Our orgranizaiton has an Exchange Ranger onsite and has opened the case with Microsoft. According to the Microsoft Entrouage support team, they have four other supports calls of the same behavior. The Entrouage team is trying to elevate it to the engineering team. I'll let you know what I learn.




Thank you so much for the info. I fill better now

I am sure I will spend next few week working on this, I will let you know if I will find anything fix before microsoft do.



Anybody find a solution this problem

I am experiencing the same exact thing. Can connect with entourage using exchange.domain.com\owa for my string but do not recieve or send mail.


I don't think anyone cares about this topic. The documentation doesn't tell you how to make Entourage work, neither the Entourage stuff on Mactopia nor in any ot the Technet stuff for Exchange 2007 that I can find. I am pretty frustrated and it seems to indicate that Microsoft doesn't seem to care that Machintoshes can't work with their Exchange servers.

I am guessing that WebDAV needs to be enabled on the CA, but I can't find one whit of helpful information on how to install and configure it. I found this: http://learn.iis.net/page.aspx/350/installing-and-configuring-webdav-on-iis-70/

but after installing WebDAV and configuring is as recommended, Entourage still doesn't work. See my 2 postings - one here about Entourage and one on Deployment about configuring WebDAV, neither of which have received any answers.

Entourage sucks, plain and simple - it should be made to work with Outlook Anywhere, but I am guessing it will be a cold day in *** before that happens..


I personally think it has something to do with the legacy folders in iis7 on server 2008 with their path locations of \\.\BackOfficeStorage\exchange.domain.edu\. the system doesnt recognize the path so how would a connecting computer know where to go. Problem is I can find anywhere better to point them.

One other question. Should an exchange 2007 server have the davx.dll and exproxy.dll files on the server.


This issue is now fixed.

We tried all sorts of things off the web and everything you could imagine.

In the end it took a phone call to Microsoft and speaking to a couple of top end techies who remoted into our servers and resolved the issue.

At first they were stumped by the problem and we had done everything right we believe, they tried several different things and reinstalling different services in different ways until it worked.


Any Idea on the combination that worked?

Hey Microsoft guys any chance we can get them to post what they did to fix it.


I had a similar issue with Entourage not working after moving to Exchange 2007. I needed to change the Exchange server name (in the Entourage account settings) to the CAS web access URL, without the /Exchange or /OWA at the end.

Entourage worked again after making that change.




I was having this same problem, Entourage 2008 was not synchronizing with Exchange 2007, only the Junk Mail folder was syncing. We discovered that in fact the problem was not the Exchange and was not the Entourage, but the redirect / exchange to / owa accounts in 2007 was not working properly.

This problem was occurring because the environment is supported on a cluster veritas, after many tests the support of Symantec guided us a procedure that resolves this problem. After completion dp procedure, the issue has been standardized, and Entourage are normally communicated with the server, thus solve the two problems. Thank you for your dedication, commitment and assistance in resolving this case. Below, following the procedure performed by Symantec for resolving the redirection:

Steps in the Cluster Veritas ambient:

Steps :

i) https://<Client_Access_Server>/owa (This is the preferred way)

ii) http://<Mailbox_Server>/Exchange or (https://<Mailbox_Server>/Exchange depending on whether SSL is configured or not.)

So if the user's mailbox is on some standalone mailbox server which does not have client access role installed, then he can not access his mail by specifying https://<Client_Access_Server>/Exchange. He will have to specify either http://<Mailbox_Sever>/Exchange or https://<Client_Access_Server>/owa. In case he specifies http://<Mailbox_Sever>/Exchange then it gets redirected to client access server's owa site.

However if the user's mailbox is on a VCS Exchange Server then it does not work. If you specify http://<EVS_NAME>/Exchange then it asks for user name and password but after that the redirection to client access server's owa site fails.

To get it working under VCS environment, the W3SVC service should be running under virtual context. So following steps need to be performed.

i) Stop the W3SVC service on both the cluster nodes. Make the startup type of this service as manual.

ii) Create a Generic service resource in Exchange Service Group for W3SVC service. Set the ‘UseVirtualName' attribute to TRUE and specify the lanman resource name for attribute ‘LanmanResName'.

iii) Set the dependency such that this resource depends on Lanman resource.

iv) Bring the resource online.

v) Start the default web site if it is not already started. (through IIS Manager).

Sorry for my poor English!

MCP - Microsoft Certified Professional
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