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Outlook Anywhere Exchange 2003 - SBS 2003 - Outlook 2007

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TimKidney

IS-IT--Management
Mar 3, 2009
16
GB
Hi all

Im trying to setup the Outlook Amywhere feature that is part of Exchange 2003 SP2 but am having issues connecting an external laptop that is running Outlook 2007.

Ive followed various guides online as well as how to set up the client but every time i connect it states "There is a problem with the proxy server's security certificate The security certificate is not from a trusted certifying authority. Outlook is unable to connect to this server"

I created a certificate for OWA using the wizard on SBS 2003 that i have Trust problems with when accessing OWA so it may be the same problem again but id like to know if i can use Outlook Anywhere with my own Certificate rather than paying for one and if so what i need to do to get Outlook to trust my Cert?

I take it that the connection side seems ok, just an issue getting past the Certificate?

Any help would be greatly appreciated.
 
Ok slight update, i found an article about manually importing the Certificates which i have done and it seems to have resolved the OWA coming up with unknown Certificate and now Outlook on the external client no longer comes up with an error about a certificate.

Instead it comes up with a login box to log on the the Exchange server.

Its now at this stage that it fails to accept any domain\user - password i enter.

Ive checked the settings and i have the Exchange server as server name.domain.local. The proxy setting is set to mail.domainname.com using SSL.

Not sure what to do next?
 
You need a trusted certificate for both OWA and OA to work correctly without either cert errors (outside your environment), or trying to push out certs via a GPO (inside your environment). Take the time to get a certificate from a trusted source.

Pat Richard MVP
Plan for performance, and capacity takes care of itself. Plan for capacity, and suffer poor performance.
 
Thanks Pat. Ok ive created a cert for my OWA address via Go Daddy, will that work for both the OWA and the Outlook Anywhere or do i need a seperate Certificate for my Server name that is entered as the Exchange server in the Outlook client setup or does it use the OWA cert when connecting to the OWA address that ive entered in the Outlook Anywhere>Proxy settings also in Outlook?
 
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