Windows/Exchange security auditing tool

From: Kevan Smith (
Date: 09/08/04

  • Next message: DeGennaro, Gregory: "RE: XP-SP2 "Feature""
    Date: Wed, 8 Sep 2004 13:08:28 -0700
    To: <>

    Note, this is a repost due to expiration of the initial post. Feel free
    to strip this line if approved. Tx.

    Exchange 2003 has no internal directory services so to speak, it uses AD
    for account maintenance, so yes Exchange 2000/2003 does require very
    fast, very reliable connectivity to a Windows 2000/2003 DC/GC.  Best
    practice recommendation is to have at least one domain controller with
    GC services in the same network segment as each Exchange back-end server
    and access to multiple DC/GCs for redundancy.  The front-end (OWA)
    server can be on a separate segment (read, separate interfaces on a
    firewall), but should maintain a solid connection to at least 1 DC/GC
    (again redundancy...).  
    The most common method of setting up OWA in a mid-size to large
    organization is to place your back-end Exchange server (hosting
    mailboxes) in the internal network or an internal DMZ with at least one
    DC/GC, then a separate front-end server in a publicly accessible DMZ.
    Lock down your ports, and make your pinholes in the firewall.
    Another method, also common in larger organizations, is to further
    isolate the front-end server behind an ISA server for further
    protections.  Fewer holes in the firewall, better SSL protection, higher
    Your concern over exposure is valid; it's the same concern which drives
    us to use UNIX based SMTP proxies.  As to the real exposure limit, keep
    OWA restricted to https and require authentication at IIS before even
    presenting the OWA logon page, and you give yourself a good level of
    protection against unauthorized access to your GAL.  
    Your remaining risk is that because your Exchange server requires access
    to your Domain Controllers, it's a potential path into your network.
    Prevent hackers from hop-scotching from a hijacked web server to the LAN
    via the OWA server by placing the OWA server in an isolated DMZ.
    Alternatively, Since you're using 2-factor authentication via
    pseudo-random numbers, force users to authenticate at the firewall
    before a single packet reaches the OWA server.  In doing this, you're
    inherently protected against unauthorized access and would then have the
    option of keeping your OWA server in the private LAN.
    There is one final alternative, which involves replicating your user
    accounts and using cross-forest authentication.  This does remove the
    direct connectivity into the network (though there is still the
    connectivity between DCs in the respective forests), but IMHO is an
    extreme measure with many hidden costs, and is not warranted in most
    Kevan S.
    MCSE, Contributing Author, MCSE Guide to Microsoft Exchange 2000 Server
    -----Original Message-----
    From: Chad Lorenc []
    Sent: Thursday, September 02, 2004 3:01 PM
    Subject: RE: Windows/Exchange security auditing tool
    I have a quick question, we are rolling out exchange 2003 with OWA.  Our
    OWA server sits one of our DMZ's, because of the active directory
    component the engineers state that OWA must be a part of our internal AD
    domain.  We currently do not have any servers bridging the internal AD
    domain into the DMZ's. 
    Is there anyway around this requirement?  
    How significant of a risk does this create, or more importantly are the
    feasible exploits past information probing?  
    We do have multiple layers of protection such as two factor
    authentication (AD login + random authenticator), host monitoring,
    firewall rules, VLAN's etc.  I am just curious, on its own, what kind of
    risk we assume with this design.
    Chad Lorenc
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  • Next message: DeGennaro, Gregory: "RE: XP-SP2 "Feature""

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