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

Posted on 2009-04-27
Medium Priority
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.
testexchangeconnectivity.com just reports a certificate error, dns and 443 connect
Server is installed and configured to enable outlook anywhere on mail.mydomain.org basic authentication
iis7 shows rcp and rcp with cert web sites
certificate is self signed mail.mydomain.org

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

ID: 24244931
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 https://host.example.com/rpc 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 16

Expert Comment

ID: 24244933
Go throught the aticle below:
Deploying Outlook Anywhere

Expert Comment

ID: 24244951

First from an internal client try to browse https://mail.mydomain.org/rpc/rpcproxy.dll 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 https://mail.mydomain.org/owa.

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


Accepted Solution

esmith69 earned 2000 total points
ID: 24244964
I am assuming above where you have "mssdt://mail.mydomain.org" is just a typo?  The correct spelling should be msstd


Featured Post

NEW Veeam Backup for Microsoft Office 365 1.5

With Office 365, it’s your data and your responsibility to protect it. NEW Veeam Backup for Microsoft Office 365 eliminates the risk of losing access to your Office 365 data.

Question has a verified solution.

If you are experiencing a similar issue, please ask a related question

If something goes wrong with Exchange, your IT resources are in trouble.All Exchange server migration processes are not designed to be identical and though migrating email from on-premises Exchange mailbox to Cloud’s Office 365 is relatively simple…
Mailbox Corruption is a nightmare every Exchange DBA wishes he never has. Recovering from it can be super-hectic if not entirely futile. And though techniques like the New-MailboxRepairRequest cmdlet have been designed to help with fixing minor corr…
In this Micro Video tutorial you will learn the basics about Database Availability Groups and How to configure one using a live Exchange Server Environment. The video tutorial explains the basics of the Exchange server Database Availability grou…
The video tutorial explains the basics of the Exchange server Database Availability groups. The components of this video include: 1. Automatic Failover 2. Failover Clustering 3. Active Manager
Suggested Courses

864 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