Post CAS 2010 install issues - Out of Office/Certificate warning.

Have just installed a new 2010 CAS and will be co-existing for a while but have a couple of issues. All mailboxes are still on 2007 mbx server and use XP/Outlook 2007. Plan is to upgrade them to Win 7/Office 2010 and migrate to new 2010 mbx server when their PC's are upgraded. Need to resolve the following issues first though.

External domain namespace is:
Internal AD domain is: companyname.local

2007 CAS: ash-owa.companyname.local
2010 CAS: cas.companyname.local

Old 2007 san certificate: (friendly name)

New 2010 SAN certificate: (friendly name)

Have installed new certificate on 2010 cas & 2007 cas.

Isuue 1: Outlook users get certificate error saying name on certificate does not match site.
If I rekey my new san certificate to include the old CAS "ash-owa.companyname.local" will this solve the issue?

Issue 2: Out of Office will not open in Outlook 2007 but can be set from OWA internally.
Is this linked with the certificate error?
nchtIT Operations ManagerAsked:
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Need to know what is the autodiscover track?

"Test email autoconfiguration" would be reaching the E2k7 and then E2010 servers from the SCP
So that should not cause the issue.

Can you share the screen-shot(s) of the "Test email autoconfiguration" log tab?
nchtIT Operations ManagerAuthor Commented:
Thanks for the reply. Test Email config result below:

Autoconfiguration has started, this may take up to a minute
Autoconfiguration found the following settings:
Display Name: Builder,Bob
Internal OWA URL: https://ash-owa.companyname.local/owa
External OWA URL:

Protocol: Exchange RPC
Server: ash-exch.companyname.local
Login Name: Bob.Builder
Availability Service URL: https://ash-owa.companyname.local/EWS/Exchange.asmx
OOF URL: https://ash-owa.companyname.local/EWS/Exchange.asmx
OAB URL: http://ash-owa.companyname.local/OAB/5fb3331d-9fc0-4455-92c4-1e968d4a042a/
Unified Message Service URL:https://ash-owa.companyname.local/UnifiedMessaging/Service.asmx
Auth Package: Unspecified
Glen KnightCommented:
You need to have both servers local fully qualified domain names in the certificate.

Do you have 2 public IP addresses?

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nchtIT Operations ManagerAuthor Commented:

Thanks for the first bit. I can re-key our SAN cetificate today.

Regarding the 2 public IP Addresses. Do you mean one each for &

Glen KnightCommented:
Yes.  The 2 public IP's are needed because Exchange 2010 doesn't proxy it redirects.  And you will need to differentiate between the source IP because you cannot forward 2 port 443's from the same IP address.
nchtIT Operations ManagerAuthor Commented:
Yes, we have all this set up although at the moment we have the address pointing back to the 2007 OWA due to an issue with mobiles.

We have around 200 smartphone users. iPhones & some nokia's were intelligent enough to change their settings to for the users mailboxes (which are still on the 2007 box). Unfortunately the android devices did not and account for 80% of our smartphones so rather than have them not working over Xmas we reverted the setting back. Have to reset the account completely on android devices so we are going to have to make a decision somewhere along the line.

Thanks for you help. Points on the way.

nchtIT Operations ManagerAuthor Commented:
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