Transition from Exch2003 to Exch 2010 cannot connect with RPC over HTTP

Posted on 2010-09-23
Medium Priority
Last Modified: 2012-05-10
We are transitioning an Organization from Exchange 2003 to Exchange 2010.
2003 is a Small Business Server, 2010 is running on Server 2008 R2 DataCenter.
Both servers are running. DNS has been updated for the new server. We have a proper certificate.
We cannot connect to using RPC HTTP/Outlook Anywhere.
Users on the LAN have no issues, we have users on both mail servers. They connect fine.
Has anyone else seen this problem, and possibly have a solution?
Question by:JamesCurrie
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Expert Comment

ID: 33748083
You enabled Outlook Anywhere, right?

Expert Comment

ID: 33748098
Also, did you try using the testexchangeconnectivity.com. That will give you some more information.
LVL 32

Expert Comment

ID: 33748102
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Author Comment

ID: 33748239
Outlook Anywhere is enabled. I will try the connectivity test.

Thanks for the link, I will test as described.

Author Comment

ID: 33752820
HI Folks,
I have gotten to a point where when connecting to the 2010 Exchange server, it prompts for a password over and over. It doesn't make a difference which server the mailbox is on 2003 or 2010, it just prompts for a password, over and over.
Any thoughts?

Assisted Solution

geieea earned 100 total points
ID: 33753417
Authentication methods are inconsistent or configure incorrectly.
LVL 11

Accepted Solution

JuusoConnecta earned 100 total points
ID: 33769306
If Outlook Anywhere is enabled, on clients computer make sure the settings are correct:

Connect to Microsoft Exchange using HTTP (checked) ->
Exchange proxy Settings -> https://webmail.yourdomain.com (is written) ->
Connect using SSL only (checked) -> Only connect to proxy servers that have this principal name in their ceritifcate (checked) -> msstd:webmail.yourdomain.com ->
Set authentication to Basic

On the server side locate -> Exchange Management console -> Server Cofiguration -> Clien Access -> Properties of your exchange server -> Outlook Anywhere -> Make youre you have your external host name written here "webmail.yourdomain.com" and Basic authentication is Set.

Make also sure that under IIS (on the exchange), sub category owa has been set for basic authenticaion

Author Comment

ID: 33801399
Thanks for the replies. I have checked out most of the suggestions, it appears that possibly the certificate we have is not working as expected. We are in the process of obtaining a new certificate.
I will update once this is done.
LVL 11

Expert Comment

ID: 33806143

If make sure that you order an SSL san ceriticate, there are several companiys that offers this, verisign among others

Author Closing Comment

ID: 33821412
Fixing the certificate issue and using the answers from geieea and JuusoConnecta has resulted in a working Exchange server.
Thank you to all who made suggestions.

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