Today I have be working on publishing Microsoft Exchange Outlook WebAccess and Active Sync to the Internet. We had some discussions with some Microsoft Consultants about a secure way to publish Outlook Web Access to the Internet, especially the authentication part of such a solution.
Some people are talking about publishing OWA directly to the Internet. In my opinion, this results in a major security thread, because you directly publish a TCP/80 and TCP/443 connection from the Exchange server to the Internet. An vulnerability or exploit in these services could end up in an hacker who takes over the Exchange server.
A second solution is placing a front-end server in a DMZ segment, but making the server a domain member for authentication. In my opinion still a security leak, because somebody who hacks the DMZ server has maybe the ability to hack or corrupt the Active Directory.
The third solution, and the solution we advise, is using a Microsoft ISA 2006 server as a front-end server in the DMZ. We configure a RADIUS or LDAPS (if you would like the option to change the password) connection to a RADIUS server or a domain member on the internal LAN segment. This ensures a secure way of authenticating users and even if somebody hacks the ISA server, he still hasn’t hacked a domain member server or a vulnerability in TCP/80 or TCP/443 of the Exchange server.
I have had a lot of help of an article on isaserver.org from Thomas Shinder while configuring the solution. I had some problems with publishing Active Sync. Ended up with enabling Basic Authentication on the Active Sync virtual directory (Microsoft-Server-ActiveSync).