Re: Exchange <--> Outlook Monitoring

["Presley, Steven" <evetsleep () gmail com>]

Unfortunately Outlook--> Exchange does not use SMTP.  It uses MAPI
(RPC) which is not plaintext (its encrypted to some degree, depending
on how the client is setup).  Because the MAPI traffic is encrypted I
think your options on sniffing the traffic to figure out what they are
sending\receiving is not going to happen.  The proper solution is
getting management\HR to approval for journaling and get your Exchange
administrators to configure the database that they are on to journal
everything to a dedicated mailbox.  I realize that you stated that
management will not approve, but unfortunately your options are
limited if you do not manage the Exchange server and if management
won't help.  In fact, is there not significant risk to your job in
trying to pull something like this off without management\HR approval?
 Most companies would not look to kindly to some one doing this
without the proper approval.

Best regards,
Steven


On Fri, 28 Jan 2005 11:28:09 -0800, Eric McCarty <eric () piteduncan com> wrote:
> Since SMTP is plain text it can be pulled off the wire @ the gateway, if
> your patient enough to use ethereal w/a filter you can pull all SMTP
> from a certain IP. Or you can use a graphical IDS like the Etrust
> product which isn't free but provides an easier and cleaner interface
> for such things.
>
> E.
>
> -----Original Message-----
> From: Doll, Josh [mailto:Doll () pbworld com]
> Sent: Friday, January 28, 2005 8:27 AM
> To: security-basics () securityfocus com
> Subject: Exchange <--> Outlook Monitoring
>
> Is there any effective way of capturing exchange / outlook data from a
> 3rd party machine?  We have a number of sub consultants with email
> access from our company, who's email needs to be monitored / archived
> for breech of contract and sharing of company secrets.  Problem is, we
> don't maintain our exchange server here in this office, and the office
> that does is unwilling to cooperate in this matter (Read: upper
> management catfight).  Therefore we need a way to ensure that what they
> send and receive is legit.  It is a relatively small number of users
> (~5) that are still on our LAN that need to be monitored, the rest have
> been moved to another subnet without company email.
>
> My understanding is that it is nowhere near as easy to capture these
> emails when it is an exchange environment vs.. the options available
> when using POP or others.
>
> Any help, or nudges in the right direction would be helpful.
>
> C. Josh Doll
> Network Administrator - Houston
> Parsons Brinckerhoff