Microsoft Windows Support

Setup Outlook Anywhere, and a friendly OWA URL

Here we'll show you how to accomplish the setup of Outlook Anywhere, and a friendly OWA URL using just one IP and one SSL certificate. The background of this topic is that the canonical hostname of a server usually is not a functional name. A functional name, such as mail usually is an friendly alias record pointing to a canonical hostname. That way, when the physical server has crashed, or for whatever reason is not available, we can point mail to another physical server with a different canonical hostname.

Our Windows server 2008 R2/Exchange 2010 server canonical DNS name is tiger.redwok.ca, with static IP 192.168.0.60. mail.redwok.ca is another name for the server, sharing the same IP.

The key here is to create a multi-hostname SSL certificate. Otherwise you would need 2 IP addresses and 2 SSL certificates. One is for the self-referential URL https://tiger.redwok.ca and the other one is for https://mail.redwok.ca. This is through the X.509 subjectAltName extension.

Finally, http://mail.redwok.ca is more user friendly than https://mail.redwok.ca. If you want to provision just https://, you can accomplish that through HTTP redirect in IIS 7.5.

Some other configurations are required to make this e-mail server fully functional even it sits on the Intranet. These configuration steps are:

1. Relay host configuration: outbound relay host and accepted domain


2. Enable and configure RPC over Https: (Server Side and Outlook client side)

Note, this setup was done in RedAnt's lab environment, so the OWA URL is not accessible from the internet. One can deploy a Exchange 2010 server directly in a DMZ, making it accessible directly from Internet. Just change the IP.