Clients cannot connect to Outlook Anywhere. Exchange 2007 SP1

Hi there,

I've been stuck on a problem relating to Outlook Anywhere. I've looked everywhere for a solution but haven't yet found anything.

Our setup is as follows (very simple at the mo as we are migrating from Exch 2003 to 2007):

1 x Exchange Server with CAS, HT, Mailbox running on Server 2008 Ent

A Comodo Unified COmms SAN certificate with:

MX Record points to

OWA works absolutely fine, no cert errors or anything.

I have enabled Outlook Anywhere after installing the RPC over HTTP feature. Didn't work, rebooted server. Still didn't work, so I uninstalled Outlook Anywhere and RPC over HTTP, rebooted and re installed.

When I try and connect with Outlook ANywhere from external it just wont accept the username and password, which is logged in the security log on the Exchange server. I have DEFINITELY got the password right :) and I have used user@internaldomain.local and internaldomain\user

When I run Test-OutlookWebServices, a number of errors appear regarding the Autodiscover Service. Error code 1013 and 1006 (I think)

If I try and set up a user who is inside the network with RPC over HTTP, it connects, but when I Ctrl-Left click on the Outlook icon and go to 'Connections' - they all say TCP IP rather than HTTPS.

I've checked the permissions in IIS and they look correct judging by various forum posts/blog entries.

Any help would be MUCH appreciated!!
Who is Participating?
MesthaConnect With a Mentor Commented:
Try it from outside using the Microsoft testing site:

When you removed the feature, did you also remove the virtual directories from IIS manager? If not then a suspect configuration can be left behind.
You need to remove the feature, remove the virtual directories, then run iisreset the write the change to the IIS metabase. Then reinstall the feature and activate it again in Exchange.

dougb9429Author Commented:
Here is the output from the test-OutlookWebServices:

[PS] C:\Windows\System32>test-outlookwebservices |fl

Id      : 1003
Type    : Information
Message : About to test AutoDiscover with the e-mail address

Id      : 1007
Type    : Information
Message : Testing server exch02.domain.local with the published name https://exch02.domain.local/EWS/Exchange.asmx &

Id      : 1019
Type    : Information
Message : Found a valid AutoDiscover service connection point. The AutoDiscover URL on this object is

Id      : 1013
Type    : Error
Message : When contacting received the error Unable to connect to
          the remote server

Id      : 1013
Type    : Error
Message : When contacting received the error A connection attempt
          failed because the connected party did not properly respond after a period of time, or established connection failed be
          cause connected host has failed to respond 123.456.789.123:443

Id      : 1006
Type    : Error
Message : The Autodiscover service could not be contacted.

I don't know if this is related to my Outlook Anywhere issue, but I thought I would post it just in case.
dougb9429Author Commented: - I've never seen that site before, but I wish I had - it helped me troubleshoot the problem and now everything is sorted - thank you so much!

Just for reference, should anyone else come across this post, it required the hotfix rollup for Exchange SP1 (I actually put rollup 5 rather than 6 as there's still a few issues with it at the mo - but rollup 4 will suffice)

We also disabled IPv6, and ensured all IIS authentication methods on the various directories were correct.

All the troubleshooting steps were provided through the site - excellent stuff.
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