[snip for brevity]

Scenario A has following disadvantages:
If your web server gets compromised, the hacker is in your internal
network. You have no means of further restricting access (besides
shutting the server down). Intrusion Detection is almost impossible
on the SSL session (unless you terminate SSL on a proxy and go clear
text from there). So a compromise can easily go undetected, and the
intruder can probe your network and advance access. The primary
intrusion containment is all of your internal network.

In Scenario B you have following advantages:
If your web server gets compromised, the hacker can access everything
in the DMZ. He will have to discover the address of the Exchange
server (which can be made hard through proper host hardening). Once
he has that he can attack the Exchange server, but using Exchange as
another stepping stone to gain access to the rest of your network can
again be very hard. All those 'hard' items will buy you time. In
addition, Intrusion Detection in the DMZ can quickly alert you if it
sees 'strange' traffic coming from the web server (say FTP
connections, port scans, etc). The primary intrusion containment is
only the DMZ.

We can even go a step further. Using a host or network based IDS
system, you can potentially reconfigure the firewall in an automated
fashion to disallow any access from/to the web server in the DMZ. Now
even the allowed ports are closed, the attacker has no way into your
network.


Scenario B buys you time and has far greater potential of protecting
your internal network.

Now, I'm primarily a security consultant, and less of an Exchange
consultant, so I may look at this differently than the average
Exchange Admin and mail list member. Reading comments like 'placing
OWA into the internal network can secure your DMZ' and 'OWA in the
DMZ opens you more up than OWA in your internal network' just make me
scream since from a security perspective, they are completely wrong.

If anyone wants to seriously discuss this further in a professional
manner, please email me offline as I'm not going to enter a silly
discussion with armchair security 'experts' on the list.

Best regards,
Frank





  We'll I'm not an expert in security, Exchange, or beermaking, but if you
told me this in a consultation, I would ask this question:

  Aren't you assuming that any hosts in the Trusted Lan in Scenario A are
completely defenseless and unmonitored, while all the hosts in the DMZ and
the trusted LAN in Scenario B are completely hardened, monitored and have
other defense systems like IDS running?  Isn't this begging the question?  

  The next question that I would have for you (and it may be one based on my
ignorance) is why is it harder (all things being equal) for a hacker to
exploit 3 or 4 different services that have holes in my firewall (NetBIOS,
RPC, SMB, etc for OWA through a DMZ) than 1 open service (HTTPS) ?

   To get my company's money, you would have to prove and document these
recomendations with independent documentation.   Saying "I'm an expert, and
no one else is" wouldn't go too far.  
 Not saying you're wrong, mind.  I just think you have to show your work to
get credit for this answer.

   Jim Helfer

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