Outlook 2007 failing to authenticate with Outlook Anywhere.  RPC over HTTP

Posted on 2009-04-27
Last Modified: 2012-05-06
I have a new exchange server 2007, everything working but Outlook Anywhere.  Basically Outlook just prompts for username and password over and over again.. as if i am entering it wrong.. I am not :)

Server config:
I have port 443 forwarding to my interior exchange server. just reports a certificate error, dns and 443 connect
Server is installed and configured to enable outlook anywhere on basic authentication
iis7 shows rcp and rcp with cert web sites
certificate is self signed

Outlook Config
My Certificate is installed Trusted Root Certificate Authorities
basic authentication
username and password same as i log into owa  

Anything i am missing.. Some permission for the user to connect somewhere.. maybe a setting in the UO group or a setting in iis 7 to allow rcp.. I have to be missing something.
Question by:brandonjel
    LVL 65

    Expert Comment

    If the test site is reporting a certificate error, then that is a problem, as certificate errors are a hard failure for this feature.

    Browse to from the machine and see what happens. You should only get an authentication prompt - which will fail, that is to be expected.

    Which authentication method do you have enabled in Exchange 2007? Basic or integrated?

    LVL 15

    Expert Comment

    Go throught the aticle below:
    Deploying Outlook Anywhere
    LVL 6

    Expert Comment


    First from an internal client try to browse and see what you get. The expected result is a Blank page. Try the same from an External Client. Make sure from external or internal client we should not get any certificate error when we trying to browse

    Try to create an Outlook Anywhere profile on an Internal Client and check the connection status to check that after configuring a profile go to Start-->Run and enter Outlook /rpcdiag

    LVL 9

    Accepted Solution

    I am assuming above where you have "mssdt://" is just a typo?  The correct spelling should be msstd


    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

    Email statistics and Mailbox database quotas You might have an interest in attaining information such as mailbox details, mailbox statistics and mailbox database details from Exchange server. At that point, knowing how to retrieve this information …
    Get an idea of what you should include in an email disclaimer with these Top 5 email disclaimer tips.
    In this video we show how to create a Shared Mailbox in Exchange 2013. We show this process by using the Exchange Admin Center. Log into Exchange Admin Center.: First we need to log into the Exchange Admin Center. Navigate to the Recipients >> Sha…
    The basic steps you have just learned will be implemented in this video. The basic steps are shown to configure an Exchange DAG in a live working Exchange Server Environment and manage the same (Exchange Server 2010 Software is used in a Windows Ser…

    730 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

    17 Experts available now in Live!

    Get 1:1 Help Now