Outlook Anywhere not working when OWA is?

hi all,

background
just finished migration from sbs 2003 to sbs 2011 with exchange 2010 installed.

External DNS is correct as is firewall as far as I can tell. outlook RPC over HTTP work when 2003 was up and running (server still in the network actually as not ready to remove yet)

outlook web access works from the world - remote.extdom.com

unfortunately when configuring outlook I get the following error

The action cannot be completed. The connection to Microsoft Exchange is unavailable. Outlook must be online or connected to complete this action.

and

Your server or mailbox names cannot be resolved.

and

There is a problem with the proxyy server's security certificate. The security certificate is not from a atrusted certifying authority. Outlook is unable to connect to the proxy server remote.extdom.co.uk (error code 8)

I am working on getting a 3rd party UCC cert which should be in place today or tomorrow but why can I not connect at all?

TIA
Gareth
Gareth McKeeCEO/OwnerAsked:
Who is Participating?
 
kpa2011Commented:
Check your autodiscovery virtual directory config. Anyway for your Outlook Anywhere to work you must have certificate properly set. Also you may want to test connectivity using remote analyzer tool.

Also below is good link to check your external connectivity.

https://www.testexchangeconnectivity.com/
0
 
James HIT DirectorCommented:
Since you are using a self-signed cert, you will need to export that cert and install it on every PC that will use Outlook Anywhere (at least until you get a proper 3rd party cert).
Outlook 2010 will not connect unless the proxy cert is a part of the trusted root certs of the local PC.
Export the cert from the Exchange server and import it into the PC and try again.
0
Question has a verified solution.

Are you are experiencing a similar issue? Get a personalized answer when you ask a related question.

Have a better answer? Share it in a comment.

All Courses

From novice to tech pro — start learning today.