PEN-200 Onboarding - A Learner Introduction Guide to the OSCP

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This article is built as a learner introduction guide to the PEN-200 course and OSCP certification. Here you will find information on:

Presentation video

What is PEN-200?

PEN-200 is a hands-on, self-study, learn-by-doing, and foundational course for pen-testing that aims to teach mindset, skills, and tools needed to increase success in InfoSec.

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PEN-200 Course Prerequisites

TCP/IP Networking Fundamentals

Operating System

Familiarity with programming/scripting languages

Try Harder Mindset

Why TRY HARDER in InfoSec?

InfoSec is continuously evolving. Techniques and tools have a shelf life. It is common to encounter unfamiliar technologies and environments during a pentest while also being expected to deliver results within a limited time frame.

It is important to have both the knowledge and disposition needed to adapt and overcome these challenges.

Try Harder disposition is timeless, once you earn it - it will never leave you.

What does it mean to TRY HARDER?

  • Trying Harder means being PERSISTENT.
  • Trying Harder means being CREATIVE.
  • Trying Harder means being PERCEPTIVE.

For more in-depth information, please see our Try Harder Blog Post.

Trying Harder means being PERSISTENT

InfoSec involves a LOT of research, troubleshooting, and testing. There are no shortcuts to success.

Mistakes and failures are part of the process. Taking a step back and understanding why the approach is failing, will help identify what to try next.

The most certain way to succeed...is always to try just one more time. In other words, try again.

Trying Harder means being CREATIVE

Repeating the same failing approach over and over is not progress. Be creative and consider different problem-solving approaches when one is not working.

You will need to use your knowledge and understanding of InfoSec concepts to consider a wide variety of solutions.

There are always different approaches to solving a problem. In other words, try differently.

Trying Harder means being PERCEPTIVE

Situational awareness is a critical skill for any Infosec professional. You must be aware of technologies, resources, and techniques available in a given situation.

It is also important to be aware of non-technical aspects such as how much time is available to you, and how best to use that time to get results. 

In other words, try smarter.

Study Approach & Tips

Study Approach (High Level)

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Learn By Doing

Practice techniques and tools that are discussed in course materials and in labs. Hands-on lab practice is key to learning success.

Buffer overflow and Active Directory involve a lot of steps and moving parts. Keep repeating labs to master the concepts and techniques involved. Replicate Alpha and Beta walkthroughs.

Master Enumeration

This one word is arguably the most important aspect of pen-testing but can be the hardest to master.

Do not simply run scans and move on. Take time to thoroughly review the output and understand its implications.

Enumeration is a cyclical approach. You will need to expand your search after each new access or new information you obtain.

Pro Tip: The more you do proper enumeration, the easier it becomes to find the proverbial “needle in a haystack”.

Read the Exploits

Try to understand how an exploit works before executing. Knowing how an exploit works even at a high level will help you debug issues you encounter.

Do you need to set up files or permissions prior to running the exploit? Do you need to modify the exploit to match your target?

Pro tip: Running unverified exploits without considering what may occur could lead to disastrous results, such as losing files.

Explore Tools

Take the opportunity to learn a wide variety of tools in labs (e.g., nmap, nikto, sshuttle, Empire, etc.). Familiarize yourself with the strengths of different tools, to identify which tool is most suited for a given situation.

Metasploit usage is limited in the PEN-200 exam, do not restrict yourself by over-utilizing Metasploit in labs.

Pro Tip: Investigate and understand how a tool works. This will help you know when and how to use the tool, and better prepare for the PEN-200 exam.

Put in Time and Effort

Depending on your background, be prepared to dedicate significant time to work through the course materials and practice in labs.

E.g., >200 - 300+ hours in the lab environment often yields the best results. 

Do not limit yourself to course materials and labs. Take the time to research any concept or prerequisite unclear to you. Google is your friend.

Practice, Practice, Practice!

There are no shortcuts in learning. The more machines you complete, the more exposure to environments and setups.

Do not rely solely on hints and walkthroughs. They are not substitute for actual learning. Attempt the machine first, at minimum.

Pro Tip: Explore machines in PG Play & Practice for additional practice, though NOT a substitute for PEN-200 lab machines.

Lab Machines Key to Success

Higher exam pass rate with >50 lab machines completed

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Getting Started

Read the course welcome email carefully. In it you will find:

  • Download links for course PDFs and videos
  • Control Panel URL
  • Help Center articles
  • VPN connectivity pack and credentials

Set up Kali Linux

  • Recommend Kali Linux with VMware Kali Linux with VMWare
  • Snapshot your VM image regularly to avoid losing your work

Connecting to PEN-200 labs

Download the "Universal VPN Package" to your Kali Linux machine.

Use the openvpn command to connect to VPN labs.

root@kali:~$ sudo openvpn universal.ovpn

For more information, visit the PEN-200 Learning Library Lab Connectivity Guide.

Lab Precautions

The lab network should be regarded as a hostile environment. We suggest using a VM to protect your host machine.

Direct VPN connection between learners is not possible. However, you may encounter exploits left by other learners. Executing these may lead to unintentional compromise of your machine.

Please be careful of unverified exploits or scripts. They may contain malicious code, resulting in the loss of your data.

Best Practices in Labs

Make sure all default passwords of your personal machines have been changed.

Avoid storing sensitive information on your Kali Linux machine in the unlikely event someone able to gain access.

You can help protect yourself by stopping services when they are in use.

Take snapshots of your personal machines regularly.

Lab Overview

The Control Panel lets you power on or revert the Challenges.

 

Lab Tip: Note Taking

  • Document Everything. Document all steps, commands, codes, and output, even those that failed. Documentation reduces rework if/when the information is later required. Notes can always be used as a reference.
  • Use Note-Taking App. Applications such as CherryTree or OneNote allow a hierarchical structure to better organize your notes.
  • Segment your notes. For instance, if attacking a single target, create sub-notes for Enumeration, Interesting finds, Exploitation, Privilege Escalation, etc.

Support

Who are Student Mentors (SMs)?

  • SMs are Offsec Alumni
  • SMs help you learn
  • SMs are your mentors
  • SMs will guide you in the right direction
    • Not give you answers
    • Will adjust guidance based on your background
  • SMs will be your friends!

When to ask SMs for help

Try course materials and labs first, and attempt to build both knowledge (technique) AND disposition (Try Harder Mindset).

Once feel you’ve exhausted and documented all steps, commands, and codes and can go no further on your own...then consider contacting SMs.

Pro Tip: SMs are here to help you build knowledge AND disposition, NOT give you the answer. They will help you find the answer on your own.

How to ask SMs for help

Be as detailed as possible. Provide all steps, commands, codes, and output when asking for help.

SMs will then understand the context and how best to assist your learning.

The guidance that SMs give is based on the amount of detail provided and your background.

The more details provided, the better SMs can assist.

Example

Bad Question:

  • Hi, I need help!
  • I need help with x.x.x.x machine

Good Question:

  • I’ve been working on getting low-level access to x.x.x.x machine. I found credentials from another machine, but they do not seem to be working. Can someone help me?
  • I’m trying to get the exploit for Lab 123 to work, however, I get an error when launching it. Here are the commands and outputs: https://paste.offsec.com/SdDfLvsw

Additional Resources

Support Channels

What Do You Need?

Learners

Offsec Community

https://portal.offsec.com/sign-in

For instruction: How may I join the Offsec Community?

Mentorship with the labs or challenge labs

VPN connectivity issues

https://chat.offsec.com/ or email help@offsec.com

Lab or exam machine testing

Exam related inquiry

challenges@offsec.com

Purchase or account related inquiry

orders@offsec.com or OSCAR (OffSec Support Chatbot Assistance Resource)

 

OSCP Preparation Guides:

Labs:

PG Play and Practice: https://www.offsec.com/labs/individual

Books:

  • Hacking: The Art of Exploitation, 2nd Edition
  • The Web Application Hacker’s Handbook
  • Black Hat Python
  • CCNA Cisco Certified Network Associate Study Guide, 7th Edition

Pentesting Reports:

Public Pentesting Reports: https://github.com/juliocesarfort/public-pentesting-reports

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