Recent upgrade of SBS2003 to Server 2K8R2 and Exchange 2010. Finally got it working... mostly but SSL and server names from intra and internet is doing my head in. I'm trying to get Outlook Anywhere working and would really like some pointers.
Here's the details:
I have a 2K8R2 AD GC and Exchange 2010 - svrname.domain.local
There are 3 other 2K3 servers still in the domain replicating DNS including the old SBS2K3 which I can't remove properly until I find the SBS discs which have been relocated in a move between offices.
I have an external domain - mydomain.com.au
I have DNS registered for mail, owa, outlook and autodiscover pointing to my public IP
I have local DNS pointers for all the above pointing to svrname
I have an EV SSL Cert from GoDaddy for owa.mydomain.com.au
I have the approriate ports on my ASA5500 open with rules for access and NAT to svrname's private IP.
Users have their Exchange accounts in the office but get certificate warnings
owa.mydomain.com.au/owa works perfectly intra and internet with secure 'green' address
My Blackberry and iPhone users have zero problems
Adding Exchange to Outlook from the Internet:
My Name, email@example.com and password entered and it starts online search for server settings.
Establishes network connection then a security alert for name mismatch autodiscover.mydomain.com.au because the certificate is owa.mydomain.com.au.
Click yes and a password request popsup for firstname.lastname@example.org, change user and enter domain\my.name and the password and get Outlook must be online error.
It then presents a Microsoft Exchange dialogue box with:
Microsoft Exchange Server: SVRNAME.domain.local
I cancel that box, it ticks searching for server settings for email@example.com then fails to logon to the server and throws the Outlook must be online error again.
Obviously I've stuffed names somewhere but I know not where. Everthing I've found online I have followed, GUI Exchange management and Exchange shell setting server names to match the certificate but nothing appears to work unless I use my basic SSL for IIS with CN: mydomain.com.au but then OWA stops working with a 403 .
Having said all that, I'm at home but can get to the office quickly (I haven't set up a VPN for RDP yet) and provide as much info as any of you may request