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RE: How to check an Executive's notebook
From: "Shenk, Jerry A" <jshenk () decommunications com>
Date: Sat, 5 Aug 2006 12:28:51 -0400

Does this guy log into the domain?  Do you have local administrator
access?  How about running something like MBSA against it from the
outside to get an initial look?

Find out what his security concerns are and maybe seed the discussion
with some of your own; Is there confidential data on your laptop?  Is
the data on your drive encrypted?  What would happen if your laptop was
stolen?  Maybe suggest booting from a Linux forensic CD (something that
mounts the drive Read Only) and see if you can view the files on his
drive.  Perhaps manually traverse the tree to his My Documents directory
and ask him if there is a file that would be ok for your to see if you
can display.

Some rather obvious things like Anti-Virus, patch levels (you might have
most of that from MBSA), personal firewall.  How about auto-run on his
CD-ROM drive...what would happen if somebody gave him a CD that
automatically ran a process that shipped data off his laptop to a
competitor?

A "High Powered Executive" is generally very time conscious and often
rather intimidating.  I think I'd develop a script ahead of time of
EXACTLY what I was planning to talk about and what I was planning to
check.  Run through EVEYRTHING ahead of time so you don't end up
fumbling around and looking like a fool.  Take notes while you're
working so that you can give him a report of what you found and some
recommendations.  Depending how "high" this guy is, it may be well worth
spending 6-8 hours ahead of time planning for a meeting with him.  I'd
also ask him for a specific amount of time, at least 30 minutes, maybe
45...if you're lucky, you might get an hour....then stick to it.  Get
your testing done ahead of time so that 5 minutes before the end of your
time, you've booted his laptop back up, asked him to log back in and
make sure everything is functioning as before...of course, you know you
didn't change anything but this will show him that you didn't change
anything and will also show your desire to avoid any possible problems.

-----Original Message-----
From: itsec.info [mailto:itsec.info () gmail com] 
Sent: Saturday, August 05, 2006 7:19 AM
To: pen-test () securityfocus com
Subject: How to check an Executive's notebook

Hi

I have a client who is a very high powered Executive and he asked me to
check 
his notebook regarding security etc.
Actually this would be any easy task but he is not willing to hand over
his 
notebook to me and I am not allowed to retrieve any data from it.

Well how can you assess such a notebook and also the person's behaviour 
regarding security (e.g. reading his private email via smtp and the
like)?

The only idea I found so far is to re-direct the notebook's Internet
traffic 
through a proxy and then I can examine this traffic and give him some
advice.

Any other ideas are very welcomed.

--
Regards,
Mike


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