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Re: What is being a pen tester really like?
From: Dogten <dogten () d3fcon org>
Date: Tue, 01 Aug 2006 20:20:37 -0500

I had a recruiter from University of Phoenix call me up the other day offering me a fast-track degree plan to make me a top security expert with their B.S in Network Security degree where I would learn how best to defend fortune 500 networks from some of the top hackers in the world and learn to examine networks just like them. It was tempting....thoughts?

dogten, CĀ²ISSP
dogten AT d3fcon DOT org

Mark Teicher wrote:
I agree and there has been many boutique consulting service shops that have been attempting to assemble a team of 
dependable, reliable, self-dressing penetration testers.  Many have failed over the years due to scaleability, lack of 
funding, some have been gobbled up by bigger and bigger corporations for pennies on the dollar due to mis-management, 
executives attempting to raise mountains out of minor little issues or exploit customers to pay lots of money for 
pen-tests that do not really address the core of the fundamental issue in the market.

There are still several people out there who 'claim' to be a "hacker" but yet never conducted a pen-test in the life or show up to a customer site late because they couldn't get up in time to make their air travel or show up to a customer looking like they just rolled out of bed or show up to make preso in camouflage pants starting their talk in hax0r language.
I learned so much from organizations and people over the years, of how to screw up a perfect good industry.  Hopefully VoIP and Vista 
security engineers learn something besides downloading eEye Retina and running against their underlying operating system and waving 
the "It's safe and secure" flag in front of everyone.

Oops, starting to sound like the guy who wrote the first firewall proxy.. Better start introducing myself to some hax0r girls at BlackHat and learn about new hax0r techniques.. Can't wait until they do a preso on basic pen-testing I bet that will be an interesting preso..


-----Original Message-----
From: FocusHacks <focushacks () gmail com>
Sent: Aug 1, 2006 10:07 AM
To: Erin Carroll <amoeba () amoebazone com>
Cc: Paul Melson <pmelson () gmail com>, rahul.joshi2 () googlemail com, pen-test () securityfocus com
Subject: Re: What is being a pen tester really like?

I agree with most of the sentiments of this thread.

Right now, anyone with some mouse skills can perform an assessment.
Nessus, Retina, Metasploit and friends are making sure of that.  That
isn't to say that automated scanning tools have no place in a
professional-grade penetration test, but people who simply run
automated tools, brand the output, and turn it over to the client are
not penetration testers, nor was that process a penetration test.

Penetration testers are a truly rare breed, and an all-out penetration
test can even be a simulation of a very real attack.  The thing to
remember is that every client will have different expectations,
different business politics to deal with, and different opinions on
what is or is not your responsibility.  You must be as flexible as you
are thorough, and as cordial as you are intelligent.

Verbal and written communication skills are a bonus.  You should be a
good public speaker and an even better technical writer.  If you are
not, then you should work alongside someone who is, and that person
should be technical enough to understand what you are talking about.

At the most basic level, you should understand that the output from
automated scanners represents POSSIBLE issues, each of which need to
be verified by hand.  If you can exploit the vulnerability without
disruption of production service, you by all means should exploit it.
Furthermore, you should also make every attempt possible to leverage
any kind of access to gain more access without causing harm.  Keep
track of things that you would like to try that might disrupt
services.  There may be a pre-production environment that you can test
on, or a maintenance window that you can utilize.

Being a real pen-tester is hard work, and it's much like having 2
full-time jobs.  Nothing stays the same for very long in the info-sec
world.  You spend just as much time researching as you do performing
the tests.  Research usually isn't limited simply to surfing
SecurityFocus lists, but that can be a significant time sink.
Research is also testing new methodologies, tools, and exploits on
your own network as well as trying to find new vulnerabilities that
have never been made public.

At the end of the day, pen-testing is a very demanding, somewhat
stressful, highly rewarding, and fast-paced job.  If you're doing it
on your own, it's a hard field to get into initially.  If you're
working for an internal audit group, you will likely be met with
opposition and animosity (especially if you are part of a company that
has thus far not HAD an internal audit group).  If you're a consultant
for a company that performs security services, you will be held to a
very high standard by both your company and your client.

Without getting your feet wet, it's hard to understand exactly what
the life of a pen-tester entails.


On 8/1/06, Erin Carroll <amoeba () amoebazone com> wrote:
Rahul,

Sadly, I have to agree with a large portion of what Paul says. Aside from
some specialised areas or situations, security assessment and penetration
tools have advanced to a point where you could get by with simply taking
canned reports and output and presenting it to your clients. IMHO, this
narrowly qualifies as true pen-testing but even without those tools
pen-testing isn't exactly rocket science.

Now being a *good* pen-tester... That's the real distinction. It's one thing
to be comfortable and proficient with pen-test tools (nessus, Core IMPACT,
Metasploit, webinspect, password tools.. the list is long) so that you can
present reliable results and recommendations. It's another thing entirely to
take those tools and wring every last ounce of performance and use from
them. Paul's Mario Andretti metaphor is a good one. The good pen-testers not
only understand and can interpret the information they gather but also
understand in detail the underlying processes and implications of what they
see (or don't see). Being able to infer from a limited dataset what
weaknesses exist and how to fully take advantage of them is not an easy
thing to pick up. It requires time, patience, experience, and a healthy dose
of paranoia. While your coding background will be of help, especially if you
want to code or modify existing exploits or tool modules, it's not as
relevant as understanding the tcp/ip stack or other more basic technical
knowledge... And being able to see the big picture from the bits and pieces
you collect.

The really rare pen-tester not only has the technical chops but can
communicate them in ways that even a 3yr old (or executive heh) could
understand. I've met people with technical depth who can run rings around me
but with very few exceptions couldn't communicate their way out of a wet
paper bag. I've also met people who are effective communicators but wouldn't
know a SYN ACK if it bit them in the nether regions. The ability to take
complex data and present it in an easy to understand format is difficult.
The fun part of pen-testing is the actual pen-testing itself... The hard
part (and the most time consuming) is writing it all down and documenting
the findings.

In my experience the day-to-day of the pen-tester experience can be summed
up pretty easily: "10 minutes of thrills followed by 10 hours of utter
boredom."

Hope that helps.


--
Erin Carroll
Moderator
SecurityFocus pen-test list
"Do Not Taunt Happy-Fun Ball"


-----Original Message-----
From: Paul Melson [mailto:pmelson () gmail com]
Sent: Friday, July 28, 2006 12:28 PM
To: rahul.joshi2 () googlemail com
Cc: pen-test () securityfocus com
Subject: RE: What is being a pen tester really like?

-----Original Message-----
Subject: What is being a pen tester really like?

rahul.joshi2 () googlemail com wrote:
I am currently a Java developer but I'm seriously thinking
of changing
paths to
a career in security and pen testing.

What I would like to know is what is being a pen tester really like?
Despite what you may have heard, being a successful
pen-tester (meaning, you get hired and make a living at it)
is not very hard, nor does it require a lot of very deep
technical skill.  What it really requires is good verbal and
written communication skills, the ability to work well with
clients, and the ability to explain security (even
inaccurately) in terms of business value.  Do those things,
and you can be successful.

The dirty truth about pen testers is that most of them have a
handful of tools and scripts (like Nessus and Retina) and run
them with the same configs against every customer and have
the same canned recommendations based on the results that
their tools spit out.  Hell, most vuln scanners spit out
their own remediation recommendations for the pen tester to
simply hand over to their customers.  Additionally, for a pen
test to have the appearance of being successful, it only
needs to find some of the vulnerabilities present on a
network or in an application.  Unlike being a network
engineer or an sysadmin where your work has to stand up to
the 24/7 scrutiny of a live environment, being a pen tester
means only needing to be right more often than you're wrong.

Not to take away from the skills or experience of any
individual pen testers out there.  There are some Mario
Andretti's out there driving school busses, if I may.


PaulM



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http://www.FocusHacks.com - The Ford Focus Modification Site!
http://www.focushacks.com/focushacks-gpg.txt - My GPG encryption key

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