Inside Entourage by Amir

A Blog Focussed on Entourage for Mac & Exchange Server

How To Setup Exchange 2007 Account Automatically in Entourage 2008 Thru Autodiscover

How To Setup Exchange 2007 Account Automatically in Entourage 2008 Thru Autodiscover

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Entourage 2008 with SP1 can use Autodiscover Service available on Exchange 2007 Server to configure your Exchange account automatically. In this post I will talk about this new feature from Entourage user perspective. I have also recorded a screencast to actually show you how you can do it in Entourage 2008. Please keep in mind that this feature is not available in earlier versions of Entourage (2004 and earlier) & Exchange (2003 & earlier).

What’s Autodiscover Service?
Microsoft Exchange Server 2007 includes a new Microsoft Exchange service named the Autodiscover service. The Autodiscover service configures client computers for Exchange mailbox access that are running Microsoft Office Outlook 2007 or Microsoft Entourage 2008 for Mac. The Autodiscover service can also configure supported mobile devices (Windows Mobile or iPhone). The Autodiscover service provides access to Microsoft Exchange features for Outlook 2007 or Entourage 2008 clients that are connected to your Microsoft Exchange messaging environment. The Autodiscover service must be deployed and configured correctly for Outlook or Entourage clients to automatically connect to Microsoft Exchange features, such as the Availability service (used for Free/Busy info pull-up), OOF Assistant and Delegate management. Additionally, these Exchange features must be configured correctly to provide their respective functionality for Outlook & Entourage clients. You can go here for more info.

Now a couple of important points:

1. Entourage Version – Check to see which version of Entourage you are using. You should be using the latest released version (build), currently its 12.1.5 (081119). In order to check for that, launch Entourage, go to ‘Entourage’ menu on top left hand corner and then click on ‘About Entourage’, the top potion of resulting window should look like this:

How To Setup Exchange Account Automatically in Entourage 2008 Thru Autodiscover-1

If your version (build) does not match, you need to install all available updates for Office 2008 for Mac. You can do that by going to ‘Help’ menu and clicking on ‘Check for Updates’. ‘Microsoft AutoUpdate’ application will launch and you can then click on ‘Check for Updates’ button there to have it look for all available updates. It will check for released updates, will come back and report to you about them and you can then install them one by one. You can also download and install all updates from Mactopia.

2. Exchange Version – Check to see which version of Exchange Server is hosting your mailbox. You can do so by logging into your mailbox thru OWA or ‘Outlook Web Access’ (explained in screencast video). Generally organizations publish a website for this purpose, like Microsoft has published this website for its employees to log into their mailboxes thru OWA. You should have one as well, if you don’t know its address or URL, you should talk to your Exchange Server Administrator or IT Help Desk/Support in your organization.

The very first mention of Exchange Server version can be found on the main login page for OWA, it looks like this if it’s not published thru Microsoft ISA Firewall Server (see ‘Microsoft Exchange’ & ‘2007’ in the screenshot below):

E2K7 OWA Login Page Mac

Screencast video also talks about this in the beginning, where OWA has been published thru Microsoft ISA Firewall Server thus the login page looks a bit different. Let’s watch the screencast now.

Note: If you meet the requirements listed above and automatic Exchange account configuration still does not work for you, then it could be because your Exchange Server Administrator has not published Autodiscover Service properly. You should then contact your administrator to verify that. You can provide this link to get him started on that.

Comments
  • How do you deal with the RTF bug between Entourage 2008 and Exchange 2007?

    In short, HTML formatted e-mail is converted to plain text e-mail when it is send to an external user.  Same e-mail sent to an "internal" emailaccount works fine (HTML keeps HTML).

  • Ronald Gros,

    Though your question does not relate to the subject of the post, I will still try my best to help you out.

    Read this post (very clear and to the point):

    http://blog.mreza.info/archive/2008/09/11/pow-1-sending-html-e-mails-to-remote-domains-via-owa-2007.aspx

    Get info on your current setting, see if that's set to MIMEText (Plain Text), if yes, set it to MIMEHtmlText (HTML), that should resolve your issue.

    For More Info:

    How to Configure Message Format Settings for a Remote Domain

    http://technet.microsoft.com/en-us/library/bb125174.aspx

    Let us know if this resolves the issue or not. Thanks!

  • Hello

    Amir

    Your blog is very great.

    AND..

    Can I download the video to my hard disk in this post ?

    Have a nice day.

  • Hi Amir,

    Great post, as usual.  We are having two issues with autodiscover in Entourage, specifically version 13.0.0 (081218), which I believe is still beta at this point.  We publish our GC using a dns record that is not the hostname, e.g. publically the GC is ldap.contoso.com, but the hostname is sf-ldap.contoso.com.  We have a commercial SSL cert with SAN entries for all names, which has been working well.  We configure our entourage clients to use "ldap.contoso.com" for the LDAP server, which is available from the internet.  "sf-ldap.contoso.com" is ONLY resolvable/available when users are on the internal network.

    The problem is that in version 13, Entourage grabs "sf-ldap" from autodiscover, which break address book lookups for external users.  When I change the setting by hand to "ldap" and quit/restart Entourage, autodiscover changes it back to "sf-ldap".  Is there a way to pass the correct ldap server name through autodiscover or tell Entourage not to override the setting?

    The second issue is that Entourage does not seem to trust the commercial cert on our ldap server, and complains that the root certificate is not valid.  We purchased the cert from Digicert, which seems to be valid on Windows boxes.  Is there a way I can tell whether the Mac natively supports our certificate chain?

  • Hi Amir,

    I have read many of your posts lately on Entourage and Exchange.  You always include great info in your blogs.  Although none of them helped me resolve the issue I was having with authentication and autodiscover, they did give me some good insight into Entourage (being recently thrust into managing Mac's in an AD environment).

    Anyway, I am wondering if there is a way to force Entourage to rerun autodiscover just as Outlook reruns it at specified intervals.

    Here is my issue, we are migrating from Exchange 2003 to Exchange 2007.  I have many Mac users using Entourage already configured to connect to the Exchange 2003 mailbox servers.  I want them to automatically pull their new mail settings from Autodiscover (yes I have confirmed this is working when setting up a new email account)so that they are pointing to my Exchange 2007 CAS servers instead of the Exchange 2003 servers which will be decommisioned after all mailboxes are moved.

    Do you have any suggestions for me?  

    Thx  

  • online game,

    I am working to redo this and other videos, I will consider your suggestion there.

    Mattfb,

    Your first issue has already been resolved, send this feedback thru Connect and you will get proper follow up with details.

    For your 2nd issue, I have seen that myself working with one customer. Entourage depends on Apple Keychain in Mac OS when it works with certificates. Look in Keychain, do you see the certificate for DigiCert CA? Match that with what you find in Windows (certmgr.msc) or use IE : Options : Content : Certificates. If proper Root CA certificate is not there in Keychain, Entourage won't be able to establish trusted SSL channel.

    jsinnwell,

    Yes, you are right, that's a known limitation of Entourage 2008 DAV Version which your users are currently using. This has been resolved in Entourage EWS (works identically to Outlook 2007 in this case), which is currently in beta, you can test it out yourself by going to: http://www.microsoft.com/mac/itpros/entourage-ews.mspx

  • Amir,

    What is your Exchange server field in Entourage?

    I am stuggling to get autodiscover working completely on my Small Business Server 2008 ed.

    Here is a full break down of what happens when Entrouage 2008 connects to the server:

    1. Start Entourage without Importing Anything

    2. Get Warning that autodiscover.domain.com is not on the certificate (currently using single domain cert and will switch it out later) Click OK.

    3. Recieves all the settings.

    4. Verifies the settings. States all are correct.

    5. Open the Entourage menu and click on Accounts

    6. Review the Exchange server line: remote.domain.com which is incorrect. Entourage 200x requires remote.domain.com/exchange/username@domain.com to function.

    All my versions of the server/client meet or excede the ones you posted screenshots on.

    How do I get entourage's autodiscover working without breaking Outlook 2007 working setup?

  • Nathaniel,

    You will need to use explicit URL (including /exchange/user@domain.com) if the underlying root domain in your environment is different than the SMTP domain (right hand side of user's default e-mail address) with which you are stamping users' default SMTP address. I am sorry but currently Entourage (using WebDAV) has no way to verify your default SMTP address or determine if root domain is different than SMTP domain. To address this situation, we published the article: http://support.microsoft.com/kb/931350

  • I bought the new Mac Book Pro with Leopard operating system and Entourage 2008 installed. I tried to configure Entourage to be as the default email program to work with Microsoft Exchange 2007 (which is installed under the Windows Server 2003 64-bit platform).  Entourage sends and receives emails using IMAP but unable to sync with the address book, Calendar, or viewing the sub files of my inbox on the exchange server. Also sometimes I get the email twice on my Mac Book but once on a windows outlook email client.  When I configured it to connect to MS Exchange Server 2007 using the “new account” – Exchange option it didn’t connect to the exchange server (basically I doesn’t bring anything from the exchange server using the exchange setup option when setting up the new account on the macbook)”.   Please not that I’ve tried the setup of Entourage 2008 (Mac Workstation and not my MacBookPro) to “another” Exchange 2007 Server 32 bit and it worked!!!

    I appreciate any help with this regards as I am new to the MAC world and I like it so far but my business and my personal productivity took a serious negative impact because of the fact that my emails or calendar are not sync.

    Much appreciated.

    Tareq.

  • Tarek,

    Configure your Exchange Account in Entourage as per the instructions in this article and it should work fine: http://support.microsoft.com/kb/931350 (using explicit URL with default SMTP/e-mail address is the key)

  • I'm having a specific issue, and was wondering if you have any insight.  I have Exch 2003 with Entourage 2008 client.  Setup and connection went smooth and is fully synch'd.  However ALL outgoing messages sent from Entourage get tagged as spam by the receiving server.  

    The reason reported is: RCVD_NUMERIC_HELO Received: contains an IP address used for HELO

    Outgoing messages work fine using Outlook or OWA.

    Could this have something to do with the domain or server name fields I used during entourage setup?  

    Or maybe I setup WebDAV access incorrectly on the server?

    Thanks for the helpful blog.

  • Mattfb,

    I am having some very similar issues to you.  We just resolved the error message where Entourage prompts you with an invalid root certificate yesterday.  We also use Digicert UC certs for our Exchange servers, and everything seemed to work fine on Windows machines. Our issue actually ended up being improper certs in both the trusted root and intermediate certificate authorities on the Exchange (CAS) side. Both these certs can be downloaded from Digicerts website.  Their tech support (and tech docs for that matter) were very helpful in resolving this issue.  It can absoutely be fixed on the server side so you do not need to make any modifications to the Mac keychain on any clients. All you need to do is delete the invalid Digicert and Entrust certs from the trusted and intermediate CA's using the MMC snapin, than import the proper certs (as downloaded from Digicerts website) into the appropriate locations.  I don't have a link to this tech doc on hand or I would supply it, but it should be fairly easily searchable, or if nothing else their tech support should be able to point you in the right direction.  

    As far as your other issue where you wanted Autodiscover to specify an externally routable DNS entry for the LDAP server, were you able to get this issue resolved?  I am actually having a similar issue in that Entourage EWS is not getting any directory (LDAP) server whatsoever.  I would like to specify a server on the autodiscover side to see if this resolves my issue.

    Thanks  

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