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Entourage 2008 will not send mail with SBS 2011

Posted on 2013-01-26
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Last Modified: 2016-06-08
Like several of the posts I have read I am still a bit confused and hope someone can give me some help. I have just migrated from SBS 2003 to SBS 2011. I have 3 users on MAcs running Entourage 2008 (not EWS). They all receive email but are unable to send email. When the try to send they get and error Labeled unknown error 170. All are accounts that are setup as Exchange accounts and the Macs have a bind on the network. They are able to log into OWA and send and receive. Pulling my harir out...................
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Question by:smccallum51
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by:browningit
browningit earned 250 total points
ID: 38822746
Here is a good explanation of what is going on:

http://technet.microsoft.com/en-us/magazine/ee681554.aspx

The important bit from the article (copypasta):

Because we have a lot of Mac users, we have a lot of Entourage 2008 (and older) clients in our Exchange 2007-based messaging environment.Most of the Entourage clients connect to Exchange using Web-Based Distributed Authoring and Versioning (WebDAV), but a few connect via Post Office Protocol (POP) as well as Internet Message Access Protocol (IMAP).

We've heard that Microsoft is discontinuing WebDAV as of Exchange 2010 and wonder if that will leave Entourage clients forced to connect to Exchange 2010 using legacy protocols such as POP or IMAP?

A       
Yes, you're right, with Exchange 2010 Microsoft discontinues WebDAV. And, yes, this means that users of Entourage 2008 and older versions will only be able to connect to Exchange 2010 via POP or IMAP.

But the Exchange team can't just ignore this mail client protocol because another Microsoft product group uses it. So, Microsoft is taking care of this problem with the new Entourage client (which, as of this writing, is in beta).

The upcoming Entourage client will use Exchange Web Services (EWS) for connecting to Exchange. As a result, this version also will support many more features than did the previous, WebDAV-based versions.

Now tasks, notes and categories can sync withExchange, and the new Entourage version will have full support for AutoDiscover (Entourage 2008 SP1 had only limited support for AutoDiscover).

You can read more about the upcoming version of Entourage here: officeformac.com/blog/Entourage-for-Exchange-Web-Services-Beta-is-Live.
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by:smccallum51
ID: 38824295
I have read in several posts abount comfiguring Entourage to connrct through OWA for Exchange 2010. Does OWA have to be published in Sharepoint App Pool ? If so can you point me in the right direction? I was able to get two of my Entourage Clients to connect to Exchange. The problem is they receive email but can not send.
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by:browningit
ID: 38824305
Everything that I have come across, including what I have posted above states that you have to use POP or IMAP for the old version of Entourage to send/receive properly.   Note from above:

"And, yes, this means that users of Entourage 2008 and older versions will only be able to connect to Exchange 2010 via POP or IMAP."

I gave it another look around and don't see anything to tell you how to send without doing this, but perhaps someone else may chime in with an answer.

Cheers,
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by:Kash
Kash earned 250 total points
ID: 38839524
have you tried authenticating as domainname\username and a password to see if that helps?
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by:
smccallum51 earned 0 total points
ID: 38845333
I came accross the following information and found to my surprise that it works......

Hey here is a heads up for all exchange 2007 and 2010 admins with a stand alone
2007 or 2010 server . By default in IIS
the /Exchange virtual directory is not created. Instead /OWA replaces
it. The /OWA will not work with Entourage 2008, it is looking for the
legacy version of owa which is by default /Exchange. You must create a
legacy virtual directory in IIS and enable WebDAV under "Web Service
Extensions"
Cheat Sheet to create a legacy virtual directory in the Exchange
Managment Shell.
This command will create a legacy Virtual Directory in IIS on the
default Website

New-OwaVirtualDirectory -name exchange -OWAVersion Exchange2003or2000 -
VirtualDirectoryType mailboxes

I would like to take credit for this, but someone else found it. This also works for SBS systems that migrated from 2003 to 2011 as I did.
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