That's an unfortunate part of the job we have to accept, yes.  Or, hire
people under you to keep an eye on it all. :)

> -----Original Message-----
> From: Cook, Jason [mailto:[EMAIL PROTECTED]] 
> Sent: Friday, June 07, 2002 5:07 PM
> To: Exchange Discussions
> Subject: RE: lesser of the evils - ssl or smtp
> 
> 
> I see.  What's your take though?  Are we babysitters or what?
> 
> Jason Cook 
> J.H. Ellwood and Associates 
> Network Administrator 
> [EMAIL PROTECTED] 
> 
> 
> -----Original Message-----
> From: Jon Butler [mailto:[EMAIL PROTECTED]] 
> Sent: Friday, June 07, 2002 4:01 PM
> To: Exchange Discussions
> Subject: RE: lesser of the evils - ssl or smtp
> 
> I was referring to DMZ's in general ...
> 
> > -----Original Message-----
> > From: Cook, Jason [mailto:[EMAIL PROTECTED]]
> > Sent: Friday, June 07, 2002 4:52 PM
> > To: Exchange Discussions
> > Subject: RE: lesser of the evils - ssl or smtp
> > 
> > 
> > What?  Can't work...so all people do all day is send emails?
> > In truth, that's all they do but it's not your job to make 
> > sure Marge in Accounting gets her baby pictures to her Mom, 
> > dig?  So what do you mean by can't work...in the context of OWA?
> > 
> > Jason Cook
> > J.H. Ellwood and Associates 
> > Network Administrator 
> > [EMAIL PROTECTED] 
> > 
> > 
> > -----Original Message-----
> > From: Jon Butler [mailto:[EMAIL PROTECTED]]
> > Sent: Friday, June 07, 2002 3:34 PM
> > To: Exchange Discussions
> > Subject: RE: lesser of the evils - ssl or smtp
> > 
> > Here's what's so sacred: your users' ability to generate
> > revenue.  It's all a matter of perspective -- to someone in a 
> > small office with a handful of users, intrustion detection 
> > and DMZs sound ridiculous, and in a lot of cases probably 
> > are.  To someone in a large enterprise envrionment with 
> > uptime requirements of 4 or 5 nine's, it's absolutely 
> > necessary and non-negotiable, and in those situations the 
> > notion of having internet traffic talking directly to an 
> > internal server is about as likely as a CEO forgiving you 
> > when 3000 of your users can't work because you thought all 
> > that extra work was "tiresome."
> > 
> > 
> > 
> > > -----Original Message-----
> > > From: Cook, Jason [mailto:[EMAIL PROTECTED]]
> > > Sent: Friday, June 07, 2002 4:21 PM
> > > To: Exchange Discussions
> > > Subject: RE: lesser of the evils - ssl or smtp
> > > 
> > > 
> > > What is it that's so sacred you're protecting.  OWA with 
> SSL through 
> > > a firewall is adequate for most places.  The mail is secure and 
> > > that's it. Gotta have credentials to get in...so that's 
> it.  DMZ is 
> > > a waste of time to me.  Constantly monitoring and patching/fixing 
> > > dmz boxes gets to be tiresome.  I mean, they're gonna get blasted 
> > > for sure and if they get taken out, so does whatever 
> service you're 
> > > running...unless they're redundant.  So what's the point? 
>  Besides, 
> > > you've opened up 80 to get to the backend Exchange box anyway.
> > > 
> > > Jason Cook
> > > J.H. Ellwood and Associates
> > > Network Administrator 
> > > [EMAIL PROTECTED] 
> > > 
> > > 
> > > -----Original Message-----
> > > From: Ragar, Russell [mailto:[EMAIL PROTECTED]]
> > > Sent: Friday, June 07, 2002 3:02 PM
> > > To: Exchange Discussions
> > > Subject: RE: lesser of the evils - ssl or smtp
> > > 
> > > 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.
> > > Not only is there off-loading of the encryption processing, 
> > > but it provides you a location for containing external 
> > > attacks.  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.  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.  Also, you 
> > > certainly couldn't scrub it easily if it were compromised.  
> > > 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.  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.
> > > 
> > > Okay, there is a cost associated with providing this type 
> of set up. 
> > > 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. 
> > > 
> > > Russell Ragar, MCSE+I, CNE, CCNA
> > > Senior Network Engineer
> > > PowerTV, Inc.
> > > 
> > > -----Original Message-----
> > > From: Chris Scharff [mailto:[EMAIL PROTECTED]]
> > > Sent: Thursday, June 06, 2002 3:05 PM
> > > To: Exchange Discussions
> > > Subject: RE: lesser of the evils - ssl or smtp
> > > 
> > > 
> > > I guess our needs here are somehwat different, perhaps.  We don't 
> > > use Exchange in the DMZ (that's ridiculous overkill) but 
> we do have 
> > > relays out there ... and we lock 'em down to specific ports 
> > > internally as well. I disagree that it would be "just as 
> harmful as 
> > > in the DMZ", though ... perform a DoS on a box in the 
> DMZ, you only 
> > > kill communications through that one box.  DoS the 
> Exchange Server, 
> > > bam -- you just lost ALL email services.
> > > 
> > > [CS] What box are you using to relay OWA that wouldn't be just as 
> > > secure on the internal network as it would be in a DMZ? I 
> can have a 
> > > dedicated OWA server in either location and the net impact to my 
> > > Exchange org seems equivalent. As to SMTP, the same thing applies 
> > > IMO. If you DoS my SMTP relay, why would the impact be 
> any greater 
> > > on my internal network than in my DMZ.
> > > 
> > > Granted, we've got more systems to support, but that's 
> the price we 
> > > pay for the security and redundancy that comes with it.
> > > 
> > > [CS] Your network seems more complex with no demonstrable 
> additional 
> > > value when compared to my configuration.... for the scenario as 
> > > asked.
> > > 
> > > And Chris, you asked to "demonstrate an exploit" ... we prefer to 
> > > not wait for one to be demonstrated, but rather do the 
> best we can 
> > > to preemptively protect ourselves before one is found: 
> use relays in 
> > > the DMZ, and mix relay products so what exploits one may not be 
> > > expoitable on another.
> > > 
> > > [CS] But that's not the scenario or question that was asked.
> > > 
> > > Have
> > > different flavors of antivirus protection at the relay, Exchange, 
> > > and at the client.
> > > 
> > > [CS] I am not opposed to an SMTP relay, it's a sound 
> idea. I don't 
> > > see much value in putting one in a DMZ really, but an 
> SMTP relay is 
> > > much different than an Exchange relay which is where this thread 
> > > started. Apples and Oranges or Horses for Courses.
> > > 
> > > Like I said before though, it ain't right for everybody 
> ... it takes 
> > > some bank to make it happen.  Our requirements here are a little 
> > > more anal than others'.
> > > 
> > > [CS] It's not about money in this case. It's about the 
> scenario as 
> > > presented.
> > > 
> > > Jon
> > > 
> > > 
> > > > -----Original Message-----
> > > > From: Webb, Andy [mailto:[EMAIL PROTECTED]]
> > > > Sent: Thursday, June 06, 2002 3:38 PM
> > > > To: Exchange Discussions
> > > > Subject: RE: lesser of the evils - ssl or smtp
> > > > 
> > > > 
> > > > On specific ports? Sure, why not?
> > > > 
> > > > I'd allow 443 to an inside box.  It requires authentication
> > > and it's
> > > > encrypted.  Any vulnerability in the application itself
> > > would be just
> > > > as harmful in the DMZ.
> > > > 
> > > > I'd allow 25 to an inside box.  The endpoint is a system
> > > that accepts
> > > > the mail and scans it for viruses and malicious content.  Any 
> > > > vulnerability in the application would be almost as
> > harmful in the
> > > > DMZ.
> > > > 
> > > > As it stands I have half the number of systems to secure in
> > > my design
> > > > as you do in yours.  If we both block 98% of the
> > vulnerabilities on
> > > > those systems, you're less secure.  I contend that I can
> > do better
> > > > than you given fewer systems to focus on.
> > > > 
> > > > Now, I'm not saying that there aren't good uses for a DMZ.
> > > There are.
> > > > Exchange just isn't one of them.
> > > > 
> > > > -----Original Message-----
> > > > From: Jon Butler [mailto:[EMAIL PROTECTED]]
> > > > Posted At: Thursday, June 06, 2002 1:53 PM
> > > > Posted To: Microsoft Exchange
> > > > Conversation: lesser of the evils - ssl or smtp
> > > > Subject: RE: lesser of the evils - ssl or smtp
> > > > 
> > > > 
> > > > So you'd allow "from any" to your inside boxes?  That
> > would keep me
> > > > awake at night. :)
> > > > 
> > > > 
> > > > > -----Original Message-----
> > > > > From: Webb, Andy [mailto:[EMAIL PROTECTED]]
> > > > > Sent: Thursday, June 06, 2002 2:47 PM
> > > > > To: Exchange Discussions
> > > > > Subject: RE: lesser of the evils - ssl or smtp
> > > > > 
> > > > > 
> > > > > but you're not talking about a good use of the DMZ.  the
> > > > DMZ should be
> > > > > an end point, not a hop.  it doesn't really matter where
> > > your SMTP
> > > > > virus scanner sits - you should have one, I agree.  but
> > > on the DMZ
> > > > > doesn't really make much difference based on your loose
> > > > restrictions
> > > > > between the DMZ and the LAN.
> > > > > 
> > > > > OWA also doesn't make much difference.  you have to 
> open up rpc 
> > > > > traffic from the DMZ to the LAN.  might as well keep
> > the DMZ more
> > > > > secure and put OWA inside.  relative security of the LAN is
> > > > about the
> > > > > same.
> > > > > 
> > > > > now, if you want to discuss multiple physical DMZ
> > > segments, perhaps
> > > > > it's more interesting, but not much.
> > > > > 
> > > > > there's quite a lot of this discussion in the archives, by
> > > > the way.
> > > > > no new arguments so far.  so, if you want to jump forward
> > > > to the end
> > > > > of the discussion, look back a couple years.
> > > > > 
> > > > > =======================================================
> > > > > Andy Webb            [EMAIL PROTECTED]      www.swinc.com
> > > > > Simpler-Webb, Inc.   Austin, TX            512-322-0071
> > > > > -- Eating XXX Chili at Texas Chili Parlor since 1989 -- 
> > > > > =======================================================
> > > > > 
> > > > > 
> > > > > -----Original Message-----
> > > > > From: Jon Butler [mailto:[EMAIL PROTECTED]] Posted At: 
> > > > > Thursday, June 06, 2002 1:30 PM Posted To: Microsoft Exchange
> > > > > Conversation: lesser of the evils - ssl or smtp
> > > > > Subject: RE: lesser of the evils - ssl or smtp
> > > > > 
> > > > > 
> > > > > Perhaps I shouldn't have used the term "rule", but rather
> > > > perhaps "a
> > > > > good security practice."  It's better to let the kiddies
> > > > play with a
> > > > > hardened DMZ bastion then your production Exchange Server
> > > ... but I
> > > > > also understand that's often not feasible for smaller
> > > companies.  A
> > > > > good security paradigm can take some dough.
> > > > > 
> > > > > 
> > > > > > -----Original Message-----
> > > > > > From: Cook, Jason [mailto:[EMAIL PROTECTED]]
> > > > > > Sent: Thursday, June 06, 2002 2:18 PM
> > > > > > To: Exchange Discussions
> > > > > > Subject: RE: lesser of the evils - ssl or smtp
> > > > > > 
> > > > > > 
> > > > > > Seems a little rash mr. butler, a lot of small
> > companies use the
> > > > > > scenario presented by Rob Ellis originally.  A
> > firewall, a good
> > > > > > hardware one anyway is great protection if used
> > > effectively.  OWA
> > > > > > with ssl is a good and secure solution, so I'm curious as
> > > > to why you
> > > > 
> > > > > > believe that it's a "rule" to use a dmz?
> > > > > > 
> > > > > > 
> > > > > > Jason Cook
> > > > > > J.H. Ellwood and Associates
> > > > > > Network Administrator
> > > > > > [EMAIL PROTECTED]
> > > > > > 
> > > > > > 
> > > > > > -----Original Message-----
> > > > > > From: Rob Ellis [mailto:[EMAIL PROTECTED]]
> > > > > > Sent: Thursday, June 06, 2002 1:06 PM
> > > > > > To: Exchange Discussions
> > > > > > Subject: RE: lesser of the evils - ssl or smtp
> > > > > > 
> > > > > > No, not remote users, server smtp traffic.
> > > > > > 
> > > > > > We are proposing citrix full desktop, OWA for some remote
> > > > users, no
> > > > > > POP/smtp access for end users.
> > > > > > 
> > > > > > The Webshield I mentioned is as you say, part of TVD.
> > > > > > 
> > > > > > Our design sounds very much like your setup.
> > > > > > 
> > > > > > 
> > > > > > Regards,
> > > > > > 
> > > > > > 
> > > > > > Rob Ellis
> > > > > > 
> > > > > > -----Original Message-----
> > > > > > From: Mellott, Bill [mailto:[EMAIL PROTECTED]]
> > > > > > Sent: 06 June 2002 18:49
> > > > > > To: Exchange Discussions
> > > > > > Subject: RE: lesser of the evils - ssl or smtp
> > > > > > 
> > > > > > Ill throw in .02
> > > > > > 
> > > > > > Assuming you are referring to allowing remote users
> > to get their
> > > > > > e-mail.
> > > > > > 
> > > > > > I'm doing the OWA thing for "remote/roaming" users.
> > > > > > I do some Citrix for full desktops.
> > > > > > I do NOT allow users to connect to the exch box at
> > this time via
> > > > > > SMTP/POP.
> > > > > > 
> > > > > > I do at this time use the Simple Webshield product
> > > > bundled with the
> > > > > > NIA/Mcafee TVD suite. It does reside on it's own machine.
> > > > > > so    Internet smtp > webshield > Exch.
> > > > > > yes the webshield sit's before Exch box.
> > > > > > Yes it provides me with an additional layer of pre 
> exch virus
> > > > > > protection...works ok yes it also provides some 
> > prefiltering on
> > > > > > attachments...sucks...does not go any deeper the first
> > > level i.e.
> > > > > > FWD> FWD it will miss.
> > > > > > Note: Their full blown product webshield APP is
> > > supposed to work
> > > > > > well..no exp with it, Ill keep my opinions to myself..
> > > > > > 
> > > > > > If I had to let  user(s) directly get to either port
> > 110/POP and
> > > > > > port25/smtp to do their e-mail...
> > > > > > 1.) I would not ..thats me..
> > > > > > 2.) Forced too only via some secure connection like a VPN.
> > > > > > 
> > > > > > bill
> > > > > > 
> > > > > > PS for those interested I run the AV product to at the
> > > file level
> > > > > > and scan all files on the exchange box with no exceptions.
> > > > > > ;-)
> > > > > > 
> > > > > > -----Original Message-----
> > > > > > From: Bendall, Paul [mailto:[EMAIL PROTECTED]]
> > > > > > Sent: Thursday, June 06, 2002 1:38 PM
> > > > > > To: Exchange Discussions
> > > > > > Subject: RE: lesser of the evils - ssl or smtp
> > > > > > 
> > > > > > 
> > > > > > Okay I'll add another spanner to your works, I would
> > > > advise an SMTP
> > > > > > relay server on your DMZ but I really wouldn't use McAfee
> > > > Webshield.
> > > > 
> > > > > > Why I hear you cry for one it is pretty bad at blocking
> > > > viruses and
> > > > > > two we have had no end of problems with it crashing or
> > > > not sending
> > > > > > to certain domains when it gets a DAT update. Why not use
> > > > the SMTP
> > > > > > component of IIS as your SMTP relay server and then use
> > > > ScanMail or
> > > > > > Antigen on your Exchange server. Either that or use
> > someone like
> > > > > > MessageLabs to outsource your antivirus too.
> > > > > > 
> > > > > > Regards,
> > > > > > 
> > > > > > Paul
> > > > > > 
> > > > > > -----Original Message-----
> > > > > > From: Rob Ellis [mailto:[EMAIL PROTECTED]]
> > > > > > Sent: 06 June 2002 18:26
> > > > > > To: Exchange Discussions
> > > > > > Subject: lesser of the evils - ssl or smtp
> > > > > > 
> > > > > > 
> > > > > > Ok, I've got a couple of scenarios, which of them is the
> > > > > least risky?
> > > > > > 
> > > > > > Exchange 2000 mailbox server on the LAN, accepting/making
> > > > > > connections using SMTP through a firewall to the internet
> > > > > > 
> > > > > > Exchange 2000 mailbox server on the LAN, accepting SSL
> > > secured OWA
> > > 
> > > > > > connections from the internet, again, protected by 
> a firewall.
> > > > > > 
> > > > > > 
> > > > > > Basically I am being told I may have to do both with
> > > the same box,
> > > 
> > > > > > but I'd rather have the smtp traffic going through a
> > DMZ based
> > > > > > gateway running McAfee Webshield, and let the OWA clients
> > > > come into
> > > > > > the internal box over SSL (which I see as less of a 
> risk than 
> > > > > > opening up port 25.
> > > > > > 
> > > > > > If you had to choose one of the 2 above scenarios, which
> > > > > would it be?
> > > > > > 
> > > > > > Regards,
> > > > > > 
> > > > > > Rob Ellis
> > > 
> > > 
> > > _________________________________________________________________
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