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PEN-200 and the OSCP

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Start with Fundamentals
LEARN ONE SUBSCRIPTION
All prerequisites for PEN-200
can be found in Network
Penetration Testing Essentials,
part of a Learn One annual
subscription.

Modules include:
Linux Basics
Network Scripting
Troubleshooting
Intro to Active Directory
Cryptography
Bash Scripting Basics

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Deepen Your Understanding
Learning Module
Learning Units
Learning Objectives
Module Exercises
Capstone Exercises

With PEN-200 (2023), each Module
has been restructured, allowing you todeepen your understanding of OffSec's
penetration testing methodology andmindset before you test your skills in
the new Challenge Labs.

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CHALLENGE YOURSELFCHALLENGE LABS
Challenge Labs are designed to help you workthrough particular penetration testing problems.
You'll encounter progressively more difficult andmore varied sets of machines with greater
complexity and dependencies.
In the final challenges, you'll have to compromisea large and rich network.

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ENGAGE WITH THE COMMUNITY
Learn from walkthroughs ofcourse Modules & Proving
Grounds machinesoffs.ec/youtube
twitch.tv/offsecofficial

Join the OffSec Community on Discord
discord.com/invite/offsec
The Importance of Community
From Jeremy Miller's Reflections on Failure, Part Two"People in information security tend to have a strong sense ofcommunity, and indeed “community” is one of OffSec’s core values. But
learning security can often feel lonely.
If I could ask one thing of the reader, it would be to please never hesitate
to reach out to others in the space for practical and emotional support –there are plenty of infosec community members who are more than
happy to help out."

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The Adversarial Mindset
Mental Models of HackersObservations of the system andits components[Ambiguity tolerance]

Recognized trends andpatterns of operation[Curiosity][Diagramming][Creativity]

Patterns of relationships
among interrelated parts
throughout the system[Domain Expertise]

Assumptions, generalizations, andimages influencing myunderstanding of the system and its
functionality

Image adapted from Summers, Timothy. How Hackers Think: A Mixed Method Study of Mental Models and Cognitive Patterns of High-Tech Wizards.
May 2015, etd.ohiolink.edu/apexprod/rws_etd/send_file/send?accession=case1427809862.

How We Teach Hacking
On one hand, we’re trying to teachtechnical information like what it means toattack web applications.
On the other, there is this whole conceptof mindset, adversarial thinking, and how
we’re going about the process.

"...hackers expressa desire and interest
in solving problems
that lack definition
and appear not tohave a solution."
Summers, Timothy. How Hackers Think: A Mixed Method Study of Mental Models
and Cognitive Patterns of High-Tech Wizards. May 2015,
etd.ohiolink.edu/apexprod/rws_etd/send_file/send?accession=case1427809862.

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Learn from Failure
From Jeremy Miller's Reflections on Failure, Part Two

Set a timer for some arbitrary amount of time,
say for three hours. Your goal is to attack achosen machine and compromise it within theallotted time.

If you are able to compromise the target, then you
have succeeded. Pick a more difficult machine or
reduce the time period and try again. At somepoint, some combination of target and time period
will inevitably cause you to fail.

When you do, write down what you havelearned during the process, and particularly
what your failed attempts might tell you
about the machine.

Your failure contributes to your global
progress and makes you a bettercybersecurity professional.

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Remember to Pauseand take aYour brain is not designed
to run non-stop.

A 5-15 minute break every
hour or so can:Improve memory
Increase productivity
Reduce stress
Reignite your creativity

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Course & Exam Resources

First PEN-200 Module

OSCP Exam with AD

OSCP Exam Prep Slides