Security Alert on Certificate on every load with Outlook 2010

Question

Each and every time I start Microsoft Office 2010 I get a Security Alert saying that there is a problem with the security certificate for autodiscover.xxx.xxx. I have followed the Certificate installation wizard to install the certificate on my machine, but even after a restart of the application I am still being prompted.

Do I have to restart the machine itself? I am using Windows 7.

Solution

Yes, the server certificate needs to be renewed. However, it also looks like that certificate does not have a Subject Alternative Name entry for autodiscover.yourdomain.com, which is the second problem shown in the screenshot.

The CAS server(s) should have at a minimum the OWA FQDN (e.g. webmail.yourdomain.com) and autodiscover (e.g. autodiscover.yourdomain.com). There are other considerations when setting up the cert request (such as load balancers, multiple datacenters, etc.)

You can use these as a references, or send to your Exchange administrator if you do not manage the infrastructure:

• http://exchangeserverpro.com/configure-an-ssl-certificate-for-exchange-server-2010
• http://technet.microsoft.com/en-us/library/dd351044(v=exchg.141).aspx