I have deployed a sbs2008 server. Originally, I purchased 1 single ssl certificate so that users could access owa remotely. That worked fine. What doesn't work fine is internal outlook 2007 clients get prompted 2 times for certificates when they connect. So researching I determined that we needed a ucc certifficate due to the changes on 2007 and use of web services...ok.So I get the certificate requested ..procured and imported and still we get prompted 2 times for certifcate issue.The error in both prompts inidcates the name is not valid or does not match the name on the certifcate. So a little more research is telling me that I may need to enable and configure an SCP in AD for Autodiscover service???? When I created ucc certificate I left autodiscover.domain.com out because i did not understand it. Is this my problem? How do I solve this issue with the certificate prompts?? My code for cert req is below. Im thinking it may be wrong AND I need to configure this autodiscover business but the light bulb just isn't lit to understand why and how, and whether this is my problem. So I put this to my colleauges and thanks for feedback in advance.
In my case my I have a .local domain and a .org external FQDN
mx record points to exchange.domain.org
sbs remote workplace is remote.domain.org
both are same ip...single static available.
My client will only use OWA and internal outlook 2007.
New-ExchangeCertificate -generaterequest -subjectname "c=us,l=Mytown, s=Mystate,
o=My Organization Name, cn=remote.domain.org" -domainname server,server.domain.local, remote.domain.org,exchange.domain.org -PrivateKeyExportable
$true -path c:\certrequest.txt