Ssl proxy and it's advantages

You could confuse continuous administration responsibilities. For instance, you may need to reconfigure your deployment to prevent supporting HTTP with SSL and proxy service provides before you can apply service packs or other improvements.

You should not simply arrange but additionally manage a certification authority (CA) and certificate trusts. You can use Certificate Services in Windows Server 2003 and Windows Server 2008, but you might not want to devote the time and resources that implementing a secure public key infrastructure (PKI) requires.