Windows Server 2012 fully updated.
IIS version 8.
Exchange 2010 fully updated.

Initially, I tried doing this with the default “HTTP Redirect.” I simply wanted to have a more generic DNS name using HTTP to redirect to the Outlook Web Access URL using HTTPS. This introduced to a couple issues. One, I needed to have SSL not be required for the “Default Web Site”, and two, I created a loop since the redirect will apply to all virtual directories below the “Default Web Site.”

I discovered the “URL Rewrite” module below:

Previously, I had used rewrite rules in Apache to accomplish a similar task, so I knew I was on the right track.

First thing you have to do is get the SSL settings right. For this I used the IIS Manager UI. I wish I had taken the time to find out how to do this with PowerShell, and here is why. For the “Default Web Site”, you open “SSL Settings” and uncheck “Require SSL.”. Now, when you do this, it will change it for all your virtual directories. So, you have select each virtual directory, open “SSL Settings”, and check “Require SSL.” Ugh.

Once that is done, install the “URL Rewrite” module. It is pretty straight forward. Once it is installed, you need to restart IIS using “iisreset”. Back in IIS Manager, select “Default Web Site” and you will notice a “URL Rewrite” icon as been added. Open it up and click “Add Rule..” under the Action menu. You give it a name, and the pattern to match. The “Action type” is “Rewrite”, and the “Rewrite URL” is where you put the HTTPS url.

Here is what I used to redirect http://mail to
Pattern: Matches the Pattern
Using: Regular Expressions
Pattern: http://mail
Ignore case: checked
No Conditions added.
No Server Variables added.
Action type: Rewrite
Rewrite URL:
Append query string: checked
Log rewritten URL: unchecked
Stop processing of subsequent rules: unchecked