Outlook Anywhere Enable\Install help.

Posted on 2008-11-04
Last Modified: 2012-05-05
Okay so I have two servers both running Server 2008, one serves as the Active Directory, and the other one is the exchange 2007. I can not for the life of me figure it out. I have followed everything I can find on the net and Outlook just disconnects when trying outlook anywhere...

I also have the same problem with the same setup using Server 2003 R2.

Any help would be great
Question by:jonnymoe
    LVL 9

    Expert Comment

    Have you purchased and installed a 3rd party SSL certificate from a Trusted Authority?
    It is fairly straightforward:

    Author Comment

    No, do you really have to do that?
    LVL 9

    Accepted Solution

    Yes, otherwise your clients will refuse the connection.  It is considered a best practice to purchase a third party cert through verisign, network solutions, etc.  Then, you don't have to worry about any configuration on the client.  However, if you want to use a self-signed certificate you can refer to the following steps:

    Here is how you generate a self-signed certificate with Exchange Server 2007 to use for Outlook Anywhere on any of your Outlook 2007 client machines:

    1. Open the Exchange Management Shell in Windows Server 2008.

    (You need to be logged in as a local Administrator and that Administrator needs to be a member of the Exchange Server Administrator group as well as the Exchange View-Only Administrators group in Active Directory. Make Administrator a member of those accounts and reboot for good measure.)

    2. Run the following commands:

    New-ExchangeCertificate -PrivateKeyExportable $True -Services IMAP, POP, IIS, SMTP -SubjectName cn=[*SEE NOTE]

    *Note: this needs to be the exact name of the external domain you are going to use to access Outlook Anywhere.

    Enable-ExchangeCertificate -Thumbprint [THUMBPRINT FROM NEW CERT]

    Export-ExchangeCertificate -Thumbprint [THUMBPRINT FROM NEW CERT] -Path C:\Certificate.pfx -Password:(Get-Credential).password

    3. Now you have a cert named Certificate.pfx sitting on C:\ on your Exchange Server. The cert is good for all of the basic Exchange 2007 services. Copy that file to any client machine you want to use to connect to Exchange Server 2007 using Outlook Anywhere.

    4. Install the certificate on your client Windows machine by going to Internet Explorer > Tools > Internet Options > Content > Certificates > Trusted Root Certificate Authorities > Import. Grab the cert you generated on your server, accept the warning dialog, and the import is successful.

    5. Run Mail from the control panel on the client machine. Add a new profile and setup an account to use an Exchange server. Type the LOCAL NAME of the Exchange server (mine was Server.home.local). Click on More Settings and navigate to the Connection tab. At the bottom of the Connection check the box next to Connect to Microsoft Exchange Using HTTP. Click on Exchange Proxy Settings. Type the name of your domain in the top URL box. Uncheck the next two boxes. Check the two boxes next to On fast networks& and On slow networks&. Set your Proxy authentication settings to use Basic Authentication. Click OK a bunch of times and you should be good to go!

    Author Closing Comment

    That was what I was missing from the net. Thank you VERY MUCH!!!!

    Featured Post

    6 Surprising Benefits of Threat Intelligence

    All sorts of threat intelligence is available on the web. Intelligence you can learn from, and use to anticipate and prepare for future attacks.

    Join & Write a Comment

    Disabling the Directory Sync Service Account in Office 365 will stop directory synchronization from working.
    This video gives you a great overview about bandwidth monitoring with SNMP and WMI with our network monitoring solution PRTG Network Monitor ( If you're looking for how to monitor bandwidth using netflow or packet s…
    In this tutorial you'll learn about bandwidth monitoring with flows and packet sniffing with our network monitoring solution PRTG Network Monitor ( If you're interested in additional methods for monitoring bandwidt…

    745 members asked questions and received personalized solutions in the past 7 days.

    Join the community of 500,000 technology professionals and ask your questions.

    Join & Ask a Question

    Need Help in Real-Time?

    Connect with top rated Experts

    16 Experts available now in Live!

    Get 1:1 Help Now