Starting a Pen-Testing Career

Starting a Pen-Testing Career

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Starting a Pen-Testing Career seraphimrhapsody 10-26-2006
Posted by on October 26, 2006, 3:36 pm
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Hello all,

This post is directed towards current network security/penetration
testing professionals.

I'm not sure what group this would be most appropriate in, so if this
is in the incorrect group, then please let me know and I'll move it
there (I've looked for a few groups that are strictly for pen-testers,
and haven't really found much). So I apologize in advance if this is
misplaced.

I'm currently a software engineer, but have a passion for network
security, and in particular penetration testing. I have to admit, I've
looked and looked for possible job descriptions for this type of work,
the pro's and con's of it, how to get into the field, etc... and
haven't found a whole lot regarding the first steps to get into this
type of industry.

I would love to have a few questions answered by those who have been
there and done this type of work. That being said, here are my
questions...

1) How did you get your start into this field of work?
1a) Did you attend any official courses to prepare?
1b) Did you obtain any certifications before you landed your first
pen-testing job?

2) What is an average day of work like for you?
2a) What are the pro's of working as a Pen-Tester?
2b) What are the con's of working as a Pen-Tester (what makes you hate
coming to work?)
2c) Do you work in a large or small firm? Or are you doing freelance
work? Which would you prefer/recommend?

3) What should I do to prepare?
3a) Are there any solid courses offered to prepare for this type of
work?
3b) What are the most credible and affordable courses one could take?
3c) In your opinion, what are the strongest certifications to have? Or
are any certifications worth their salt?

4) Are there any websites out there that would have some or all of the
answers to the questions above?

I've looked into going to the InfoSec school for Ethical Hacking, and
would love to have the bootcamp style training to get me started, but
atm, the cost is a bit outside of my limits. I can say, though, that
sometime next year I will be able to take such a course. In the
meantime, though, I'm trying to figure out if this is something that
I'd like to pursue. I currently have a very secure job and am quite
happy with it (most days :) ), as well as having a very bright future
for advancement in the industry, but I'm pretty sure I would absolutely
love this type of work. I feel like I've only read 'hype' about the
career, though. I'd love to pick a grizzled veteran's brain about this
and see if it's the right career move for me. Also, I'm young enough to
make a career switch a viable option. So it's been weighing on my mind
pretty heavily as of late, heh.

Thanks in advance to all reply with anything useful,
Keith


Posted by on October 26, 2006, 4:18 pm
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seraphimrhapsody@gmail.com wrote:
> 1) How did you get your start into this field of work?
> 1a) Did you attend any official courses to prepare?
> 1b) Did you obtain any certifications before you landed your first
> pen-testing job?

Nope. Nope. I transfered within a large company I was already
working for.

> 2) What is an average day of work like for you?

Walk down the hall, login to the computer. Break something new every
week or so. Short engagements, lots of new stuff all the time.
Always learning.

> 2a) What are the pro's of working as a Pen-Tester?

It's a lot more fun and rewarding to break stuff than to have to deal
with all the tedium of having to create things for the lowest common
denominator to use.

> 2b) What are the con's of working as a Pen-Tester (what makes you hate
> coming to work?)

When customers have you reassess their stuff a year later and all the
same stuff you reported a year ago is still broken. That's about it
though. It's a dream job.

> 2c) Do you work in a large or small firm? Or are you doing freelance
> work? Which would you prefer/recommend?

I'm in a large one. It has its benefits and detriments. A small firm
arguably can be more aggressive in their testing as they're not as
large a target for getting sued should something go horribly wrong.
Hasn't happened of course, but just htinking out loud. A large firm
has all the resources of a large firm, and an established brand that
connotes trust with a customer and applied appropriately, a steady
stream of business. Education budgets, lots of network
infrastructure and all that jazz. Smaller outfits mean more
uncertainty but generally higher salaries, less to invest in education
perhaps, less places to go if you ever get burned out.

This question I think is largely orthogonal of the profession and more
a personal choice regardless of your IT specialty I guess. Also
depends a lot on the individual company.

> 3) What should I do to prepare?

Send me your resume. I'll see if there's a fit.

If you aren't already very comfortable in both Linux and Windows, get
comfortable in both.

> 3a) Are there any solid courses offered to prepare for this type of
> work?

Oh yes. That Infosec CEH class you mention later is pretty darned
good. They have an advanced class as well that includes exploit
coding...and I think your background would make you very interested in
that.

Defcon is a decent cheap conference that's held annually.

> 3b) What are the most credible and affordable courses one could take?
> 3c) In your opinion, what are the strongest certifications to have? Or
> are any certifications worth their salt?

CISSP is probably the most widely known, but it requires someone with
a CISSP to certify that you've worked in a security related field for
a givne amount of time. Your work as a software developer though can
be construed in that way however. Make friends with a CISSP.

SANS.org GIAC certifications are a little more highly regarded I'd say
but cost will be an issue there as well, and then there's the issue of
which one to take. I don't know that I'd recommend it as a first
step.

> 4) Are there any websites out there that would have some or all of the
> answers to the questions above?
>
> I've looked into going to the InfoSec school for Ethical Hacking, and
> would love to have the bootcamp style training to get me started, but
> atm, the cost is a bit outside of my limits.

Talk with them see what you can negotiate. It's a good class, a very
good organization (Jack's awesome) and the EC Council certification
will carry some weight too. I haven't tested mine out in the
marketplace, so it's hard to say.

> I can say, though, that sometime next year I will be able to take
> such a course. In the meantime, though, I'm trying to figure out if
> this is something that I'd like to pursue.

Sounds like a great fit for your interests.

> I currently have a very secure job and am quite happy with it (most
> days :) ), as well as having a very bright future for advancement in
> the industry, but I'm pretty sure I would absolutely love this type
> of work. I feel like I've only read 'hype' about the career,
> though.

If you ask me, the hype is real. It's very fun to break stuff for a
living.

> I'd love to pick a grizzled veteran's brain about this and see if
> it's the right career move for me. Also, I'm young enough to make a
> career switch a viable option. So it's been weighing on my mind
> pretty heavily as of late, heh.

Security is still very much a growth industry and I dont' see that
changing any time soon. Versus software development, if you're living
in the US, there's an argument to be made that folks will be less
prone to offshore their security assessment work than they would code
and software engineering.

> Thanks in advance to all reply with anything useful,

Dunno if I've tripped that level, but yer welcome retroactively, as
applicable. :-)

--

http://www toddh net/

Posted by erewhon on October 28, 2006, 1:14 am
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> 2) What is an average day of work like for you?

As someone on the end of reading security audit reports, can you:

1 - write high-level management reports, with scare stories to generate more
work?

2 - can you write down all the issues their own tech team tell you are
issues, and present this as your own work?

3 - can you state the bleeding obvious in an important-looking document -
'you need to patch your systems, have firewalls & IDS, do more monitoring,
QA your software, run up-to-date AV, limit admin accts, enforce password
policy, limit physical access, review security logs....'. (Since every firm
is always just one step behind in some area, you will always find an 'in').
If they are fully up-to-date and compliant, can you scare them with 0-day
exploits and more consultancy costs.

4 - can you steer someone else's cleverly written vulnerability scanner, and
produce reams of pdf reports which justifies your pointless exercise and
substantial contract fee

If so, go work for a big audit firm and keep reselling the above and keep
creaming the profits, whilst knowing in your heart you've never written a
line of exploit code or had an original idea on security yourself.

erewhon
alt.hacker



Posted by Todd H. on October 28, 2006, 1:34 am
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> > 2) What is an average day of work like for you?
>
> As someone on the end of reading security audit reports, can you:
>
> 1 - write high-level management reports, with scare stories to generate more
> work?
>
> 2 - can you write down all the issues their own tech team tell you are
> issues, and present this as your own work?
>
> 3 - can you state the bleeding obvious in an important-looking document -
> 'you need to patch your systems, have firewalls & IDS, do more monitoring,
> QA your software, run up-to-date AV, limit admin accts, enforce password
> policy, limit physical access, review security logs....'. (Since every firm
> is always just one step behind in some area, you will always find an 'in').
> If they are fully up-to-date and compliant, can you scare them with 0-day
> exploits and more consultancy costs.
>
> 4 - can you steer someone else's cleverly written vulnerability scanner, and
> produce reams of pdf reports which justifies your pointless exercise and
> substantial contract fee


Pity.

Sounds like you have contracted someone doing vulnerability scanning
vs actual ethical hacking.

But it's funny cus the market does have a lot of such crap out there.

Best Regards,
--
Todd H.
http://www.toddh.net/

Posted by erewhon on October 28, 2006, 1:36 am
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> Pity.
>
> Sounds like you have contracted someone doing vulnerability scanning
> vs actual ethical hacking.

From a company perspective, they just want a report which tells them what
their exposures are (which any idiot could tell them - see point 3), and
then they can justify the spend and action the recommendations, and thereby
cover their ass should anyone externally need to have proof of their
'security'

It's not about hacking into code, it's about ticking the boxes.

> But it's funny cus the market does have a lot of such crap out there.

Ususally with a big brand name and a ludicrous fee



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