Autodiscover, Out of Office and Wildcard SSL

[Anonymous]

#154284

Background:

Our Exchange 2010 server uses a wildcard SSL certificate
*.PublicDomain.com

The exchange server has CAS, Hub Transport and Mailbox roles.

The exchange server is installed on a resource domain
mailserver.mail.local

The mailboxes are Linked Mailboxes, with LinkedMasterAccount set to their windows logon account within a trusted domain
LogonDomainSome.Guy

Outlook clients have been manually configured, pointing to the mail server via internal FQDN:
mailserver.mail.local

Issue:

When trying to get into Out of Office settings in Outlook, the following error is displayed:
“Your Out of Office settings cannot be displayed, because the server is currently unavailable. Try again later”

Troubleshooting:

Everything seems to point to Autodiscover not being set up correctly and OOF relying on this service.

This sounded right, seeing as I hadn’t done any work on Autodiscover and all client workstations were configured manually.

Changes made:

I’ve now set up an A record on our public DNS to try and get Autodiscover and OOF working.

A record:
autodiscover.publicdomain.com -> public IP address for Exchange server

I set up an A record on our internal DNS:
autodiscover.publicdomain.com -> internal IP address for Exchange Server

Result:

Test exchange connectivity says Autodiscover is OK

Out of Office error remains unchanged.

All client PC’s are throwing an SSL security alert because mailserver.mail.local has a security certificate which does not match the name on certificate.
(*.publicdomain.com)

I’m out of my depth on this and have a lot of people angry at me

[Author]

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