When you launch Outlook it throws the following error "Information you exchange with this site cannot be viewed or changed by others. However, there is a problem with the site's security certificate. The name on the security certificate is invalid or does not match the name of the site." I noticed from the error message that the Outlook client was trying to
connect to mail.domain.local which I was surprised to see as all of the
Virtual Directories should have been configured to use the mail.domain.com
address. The Exchange 2013 certificate currently being used was sourced from a Public
Certificate Authority and therefore did not have the .local suffix
within it, therefore the error made perfect sense.
The first step was to reconfigure the Virtual
Directories for AutoDiscover and Outlook Anywhere to confirm they
were using the mail.domain.com FQDN. The following PowerShell command
can be used to set the Internal AutoDiscover URL;
The Outlook Anywhere directories can be
configured using the ECP, click on Servers and then Servers again
click the Client Access (CAS) servers and use the Pencil tool to open
the configuration window. Click Outlook Anywhere and ensure the
directories are set to mail.domain.com.
I then created an SVR DNS Records for AutoDiscover,
this is done using DNS Manager. Right click on the Forward Lookup
Zone for your domain and select Other Resource Record, scroll down
and select Service Location (SRV) and
click Create Record...
Fill in the New Resource Record details as
shown below.
Expand you domain and then _tcp and you
should see an SVR Record for _autodiscover.
Now if you re-launch Outlook there are no
certificate errors. Although this worked for me in this instance due to the
broad nature of this error this may not off course resolve the issue in your
environment.