-----Original Message----- 
Regarding Outlook Web Access deployments, particularly with Exchange
2000, I can see a large benefit to deploying a front end server in the
DMZ which communicates to the Internet client using SSL and the backend
mailbox servers over HTTP.  

CS: Specifically over a FE server on the internal network?

Not only is there off-loading of the
encryption processing,

CS: Apparently not over a FE server on the internal network. I too can
compare apples and pears and claim an apple is a woefully inadequate pear.

 but it provides you a location for containing
external attacks. 

CS: How specifically are they contained when between my FE server and my
other E2K servers/AD/DNS servers there are a host of ports open, including
quite possibly the ports which you used to run your original exploit.

 Yes, in a sense, all servers in the DMZ are
sacrificial victims.  The theory is that you keep your sacrificial
victims in a contained area so they can be monitored carefully and you
fall back and reformat them as soon as they are compromised.

CS: What are we using to monitor this box specifically and what exploit did
we use to access the box in the first place (any Exchange version 443 based
exploit) that our IDS is going to detect the behavior and alert us?

  Obviously
you need both intrusion detection and host-based firewalling with the
DMZ (to prevent compromise of the DMZ from host to host).  If there were
no front-end server (direct OWA access on the mailbox server) you
couldn't possibly monitor it as well since it is performing many more
functions.  

CS: This post began with the question of what is the advantage of a
particular server in a DMZ. Changing the equation to say 'if we add this,
that and the other, and implement a DMZ we'll be more secure than if we just
publish our password on the internet' is silly. 

Also, you certainly couldn't scrub it easily if it were
compromised. 

CS: IBID

 If you were running a front-end server internally
(no-DMZ), if that box were compromised it could be used as a staging
area for an attack on all your internal systems.  

CS: And the FE server in my DMZ couldn't? Puhleese.

So, yes, the
assumption is that all machines in your DMZ will eventually be
compromised and they are suspect.  

Okay, given my recommended configuration, the essential problem is that
the front-end server has to have access to some key internal services in
order to function. The trick would appear to be to lock down those
internal services as much as possible and to get a really good intrusion
detection system that will allow you to shutdown your front-end server
access to internal services as quickly as possible.  

CS: And I couldn't harden my FE server on the internal network in the exact
same way? What would be the net increased risk if I were to do so?

Okay, there is a cost associated with providing this type of set up.

CS: Ignore cost, it's a red herring thrown up to say... if I spend more
money than you, I can design a more secure system then you. If I spend the
same amount of $ and have the same basic config except my FE server is in my
internal network specifically and demonstrably how am I less secure?

You can't run a front-end server on Exchange 2000 Standard, you'll need
Enterprise.  You'll need a good firewall.  You'll need good virus
protection, host-based firewalls, and an intrusion detection system
(network defenses without intrusion detection is like a city wall with
no night watch).  None of this is cheap, but that's the price of using
OWA on the Internet.  If you don't have the money to do it securely,
don't provide the service. 

CS: I'm using OWA on the internet and am quite content with my current
configuration/ risks. I don't see how simply placing my OWA server in the
DMZ will make it more secure and your post, while interesting in a 'it's
redundant because it's been covered ad infinitum in the archives' kind of
way is purely theoretical and demonstrates no intrinsic value gained
specifically from the placement of the Exchange server in a DMZ in my mind.

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