OffSec PEN-200 (OSCP)

All learners are required to have:

• Solid understanding of TCP/IP networking
• Reasonable Windows and Linux administration experience
• Familiarity with basic Bash and/or Python scripting

Who is this course for.

• Infosec professionals transitioning into penetration testing
• Pen testers seeking one of the best pentesting certifications
• Those interested in pursuing a penetration tester career path
• Security professionals
• Network administrators
• Other technology professionals

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Bring Your Own Device

Learners must bring their own laptop to take part in this class.

Minimum hardware specification:

• CPU: 64-bit Dual Core (2.2 GHz per core)
• RAM: 8 GB (Recommended)
• Display resolution: 1024×768
• HDD: Minimum 20GB available space

Minimum software requirements:

• Operating system: Windows 8.1 x64 / OSX Yosemite / MacOS/Kali 2017.x/ Debian 9.3/Ubuntu 17.10*
• Virtualization Software: VMware Player (Latest version), VMware Workstation 8.0, VMware Fusion 7.0

Module 1 - Penetration Testing with Kali Linux : General Course Introduction

Welcome to PWK

• Take inventory over what’s included in the course
• Set up an Attacking Kali VM
• Connect to and interact over the PWK VPN
• Understand how to complete Module Exercises

Module 2 - Introduction to Cybersecurity

The Practice of Cybersecurity

• Recognize the challenges unique to information security
• Understand how 'offensive' and 'defensive' security reflect each other
• Begin to build a mental model of useful mindsets applicable to information security

Threats and Threat Actors

• Understand how attackers and defenders learn from each other
• Understand the differences between risks, threats, vulnerabilities, and exploits
• List and describe different classes of threat actor
• Recognize some recent cybersecurity attacks

The CIA Triad

• Understand why it's important to protect the confidentiality of information
• Learn why it's important to protect the integrity of information
• Explore why it's important to protect the availability of information

Security Principles, Controls, and Strategies

• Understand the importance of multiple layers of defense in a security strategy
• Describe threat intelligence and its applications in an organization
• Learn why access and user privileges should be restricted as much as possible
• Understand why security should not depend on secrecy
• Identify policies that can mitigate threats to an organization
• Determine which controls an organization can use to mitigate cybersecurity threats

Cybersecurity Laws, Regulations, Standards, and Frameworks

• Gain a broad understanding of various legal and regulatory issues surrounding cybersecurity
• Understand different frameworks and standards that help organizations orient their cybersecurity activities

Career Opportunities in Cybersecurity

• Identify career opportunities in cybersecurity

Module 3 - Effective Learning Strategies

Learning Theory

• Understand the general state of our understanding about education and education theory
• Understand the basics of memory mechanisms and dual encoding
• Recognize some of the problems faced by learners, including 'The Curve of Forgetting' and cognitive load

Unique Challenges to Learning Technical Skills

• Recognize the differences and advantages of digital learning materials
• Understand the challenge of preparing for unknown scenarios
• Understand the potential challenges of remote or asynchronous learning

OffSec Methodology

• Understand what is meant by a Demonstrative Methodology
• Understand the challenge of preparing for unknown scenarios
• Understand the potential challenges of remote or asynchronous learning

Case Study: chmod -x chmod

• Review a sample of learning material about the executable permission, expand beyond the initial information set, and work through a problem
• Understand how OffSec's approach to teaching is reflected in the sample material

Tactics and Common Methods

• Learn about Retrieval Practice
• Understand Spaced Practice
• Explore the SQ3R and PQ4R Method
• Examine the Feynman Technique
• Understand the Leitner System

Advice and Suggestions on Exams

• Develop strategies for dealing with exam-related stress
• Recognize when you might be ready to take the exam
• Understand a practical approach to exams

Practical Steps

• Create a long term strategy
• Understand how to use a time allotment strategy
• Learn how and when to narrow your focus
• Understand the importance of a group of co-learners and finding a community
• Explore how best to pay attention and capitalize on our own successful learning strategies

Module 4 - Report Writing for Penetration Testers

Understanding Note-Taking

• Review the deliverables for penetration testing engagements
• Understand the importance of note portability
• Identify the general structure of pentesting documentation
• Choose the right note-taking tool
• Understand the importance of taking screenshots
• Use tools to take screenshots

Writing Effective Technical Penetration Testing Reports

• Identify the purpose of a technical report
• Understand how to specifically tailor content
• Construct an Executive Summary
• Account for specific test environment considerations
• Create a technical summary
• Describe technical findings and recommendations
• Recognize when to use appendices, resources, and references

Module 5 - Information Gathering

The Penetration Testing Lifecycle

• Understand the stages of a Penetration Test
• Learn the role of Information Gathering inside each stage
• Understand the differences between Active and Passive Information Gathering

Passive Information Gathering

• Understand the two different Passive Information Gathering approaches
• Learn about Open Source Intelligence (OSINT)
• Understand Web Server and DNS passive information gathering

Active Information Gathering

• Learn to perform Netcat and Nmap port Scanning
• Conduct DNS, SMB, SMTP, and SNMP Enumeration
• Understand Living off the Land Techniques

Module 6 - Vulnerability Scanning

Vulnerability Scanning Theory

• Gain a basic understanding of the Vulnerability Scanning process
• Learn about the different types of Vulnerability Scans
• Understand the considerations of a Vulnerability Scan

Vulnerability Scanning with Nessus

• Install Nessus
• Understand the different Nessus Components
• Configure and perform a vulnerability scan
• Understand and work with the results of a vulnerability scan with Nessus
• Provide credentials to perform an authenticated vulnerability scan
• Gain a basic understanding of Nessus Plugins

Vulnerability Scanning with Nmap

• Understand the basics of the Nmap Scripting Engine (NSE)
• Perform a lightweight Vulnerability Scan with Nmap
• Work with custom NSE scripts

Module 7 - Introduction to Web Applications

Web Application Assessment Methodology

• Understand web application security testing requirements
• Learn different types of methodologies of web application testing
• Learn about the OWASP Top10 and most common web vulnerabilities

Web Application Assessment Tools

• Perform common enumeration techniques on web applications
• Understand Web Proxies theory
• Learn how Burp Suite proxy works for web application testing

Web Application Enumeration

• Learn how to debug Web Application source code
• Understand how to enumerate and inspect Headers, Cookies, and Source Code
• Learn how to conduct API testing methodologies

Cross-Site Scripting (XSS)

• Understand Cross-Site Scripting vulnerability types
• Exploit basic Cross-Site Scripting
• Perform Privilege Escalation via Cross-Site Scripting

Module 8 - Common Web Application Attacks

Directory Traversal

• Understand absolute and relative paths
• Learn how to exploit directory traversal vulnerabilities
• Use encoding for special characters

File Inclusion Vulnerabilities

• Learn the difference between File Inclusion and Directory Traversal vulnerabilities
• Gain an understanding of File Inclusion vulnerabilities
• Understand how to leverage Local File Inclusion (LFI to obtain code execution
• Explore PHP Wrapper usage
• Learn how to perform Remote File Inclusion (RFI) attacks
• Understand File Upload Vulnerabilities
• Learn how to identify File Upload vulnerabilities

File Upload Vulnerabilities

• Explore different vectors to exploit File Upload vulnerabilities

Command Injection

• Learn about command injection in web applications
• Use operating system commands for OS command injection
• Understand how to leverage command injection to gain system access

Module 9 - SQL Injection Attacks

SQL Theory and Database Types

• Refresh SQL theory fundamentals
• Learn different DB types
• Understand different SQL syntax

Manual SQL Exploitation

• Manually identify SQL injection vulnerabilities
• Understand UNION SQLi payloads
• Learn about Error SQLi payloads
• Understand Blind SQLi payloads

Manual and Automated Code Execution

• Exploit MSSQL Databases with xp_cmdshell
• Automate SQL Injection with SQLmap

Module 10 - Client-Side Attacks

Target Reconnaissance

• Gather information to prepare client-side attacks
• Leverage client fingerprinting to obtain information

Exploiting Microsoft Office

• Understand variations of Microsoft Office client-side attacks
• Install Microsoft Office
• Leverage Microsoft Word Macros

Abusing Windows Library Files

• Prepare an attack with Windows library files
• Leverage Windows shortcuts to obtain code execution

Module 11 - Locating Public Exploits

Getting Started

• Understand the risk of executing untrusted exploits
• Understand the importance of analyzing the exploit code before execution

Online Exploit Resources

• Access multiple online exploit resources
• Differentiate between various online exploit resources
  • Understand the risks between online exploit resources
  • Use Google search operators to discover public exploits

Module 12 - Locating Private Exploits

Offline Exploit Resources

• Access Multiple Exploit Frameworks
• Use SearchSploit
• Use Nmap NSE Scripts

Exploiting a Target

• Follow a basic penetration test workflow to enumerate a target system
• Completely exploit a machine that is vulnerable to public exploits
• Discover appropriate exploits for a target system
• Execute a public exploit to gain a limited shell on a target host

Module 13 - Fixing Exploits

Fixing Memory Corruption Exploits

• Understand high-level buffer overflow theory
• Cross-compile binaries
• Modify and update memory corruption exploits

Fixing Web Exploits

• Fix Web application exploit
• Troubleshoot common web application exploit issues

Module 14 - Antivirus Evasion

Antivirus Evasion Software Key Components and Operations

• Recognize known vs unknown threats
• Understand AV key components
• Understand AV detection engines

AV Evasion in Practice

• Understand antivirus evasion testing best practices
• Manually evade AV solutions
• Leverage automated tools for AV evasion

Module 15 - Password Attacks

Attacking Network Services Logins

• Attack SSH and RDP Logins
• Attack HTTP POST login forms

Password Cracking Fundamentals

• Understand the fundamentals of password cracking
• Mutate Wordlists
• Explain the basic password cracking methodology
• Attack password manager key files
• Attack the passphrase of SSH private keys

Working with Password Hashes

• Obtain and crack NTLM hashes
• Pass NTLM hashes
• Obtain and crack Net-NTLMv2 hashes
• Relay Net-NTLMv2 hashes

Module 16 - Windows Privilege Escalation

Enumerating Windows

• Understand Windows privileges and access control mechanisms
• Obtain situational awareness
• Search for sensitive information on Windows systems
• Find sensitive information generated by PowerShell
• Become familiar with automated enumeration tools

Leveraging Windows Services

• Hijack service binaries
• Hijack service DLLs Abuse Unquoted service paths

Abusing other Windows Components

• Leverage Scheduled Tasks to elevate our privileges
• Understand the different types of exploits leading to privilege escalation
• Abuse privileges to execute code as privileged user accounts

Module 17 - Linux Privilege Escalation

Enumerating Linux

• Understand files and user privileges on Linux
• Perform manual enumeration
• Conduct automated enumeration

Exposed Confidential Information

• Understand user history files
• Inspect user trails for credential harvesting
• Inspect system trails for credential harvesting

Insecure File Permissions

• Abuse insecure cron jobs to escalate privileges
• Abuse Insecure file permissions to escalate privileges

Insecure System Components

• Abuse SUID programs and capabilities for privilege escalation
• Circumvent special sudo permissions to escalate privileges
• Enumerate the system’s kernel for known vulnerabilities, then abuse them for privilege escalation

Module 18 - Advanced Tunneling

Tunneling Through Deep Packet Inspection

• Learn about HTTP tunnelling
• Perform HTTP tunneling with Chisel
• Learn about DNS tunneling
• Perform DNS tunneling with dnscat

Module 19 - The Metasploit Framework

Getting Familiar with Metasploit

• Setup and navigate Metasploit
• Use auxiliary modules
• Leverage exploit modules

Using Metasploit Payloads

• Understand the differences between staged and non-staged payloads
• Explore the Meterpreter payload
• Create executable payloads

Performing Post-Exploitation with Metasploit

• Use core Meterpreter post-exploitation features
• Use post-exploitation modules
• Perform pivoting with Metasploit

Automating Metasploit

• Create resource scripts
• Use resource scripts in Metasploit

Module 20 - Active Directory Introduction and Enumeration

Active Directory Manual Enumeration

• Enumerate Active Directory using legacy Windows applications
• Use PowerShell and .NET to perform additional AD enumeration

Manual Enumeration Expanding our Repertoire

• Enumerate Operating Systems Permissions and logged on users
• Enumerate Through Service Principal Names
• Enumerate Object Permissions
• Explore Domain Shares

Active Directory Automated Enumeration

• Collect domain data using SharpHound
• Analyze domain data using BloodHound

Module 21 - Attacking Active Directory Authentication

Understanding Active Directory Authentication

• Understand NTLM Authentication
• Understand Kerberos Authentication
• Become familiar with cached AD Credentials

Module 22 - Attacking Active Directory Authentication

Performing Attacks on Active Directory Authentication

• Use password attacks to obtain valid user credentials
• Abuse the enabled user account options
• Abuse the Kerberos SPN authentication mechanism
• Forge service tickets
• Impersonate a domain controller to retrieve any domain user credentials

Module 23 - Lateral Movement in Active Directory

Active Directory Lateral Movement Techniques

• Understand WMI, WinRS, and WinRM lateral movement techniques

• Abuse PsExec for lateral movement

• Learn about Pass The Hash and Overpass, The Hash as lateral movement techniques

• Misuse DCOM to move laterally

Active Directory Persistence

• Understand the general purpose of persistence techniques

• Leverage golden tickets as a persistence attack

• Learn about shadow copies and how they can be abused for persistence

Module 24 - Assembling the Pieces

Enumerating the Public Network

• Enumerate machines on a public network

• Obtain useful information to utilize for later attacks

Attacking WEBSRV1

• Utilize vulnerabilities in WordPress Plugins

• Crack the passphrase of a SSH private key

• Elevate privileges using sudo commands

• Leverage developer artifacts to obtain sensitive information

Gaining Access to the Internal Network

• Validate domain credentials from a non-domain-joined machine

• Perform phishing to get access to internal network

Enumerating the Internal Network

• Gain situational awareness in a network

• Enumerate hosts, services, and sessions in a target network

• Identify attack vectors in target network

Attacking the Web Application on INTERNALSRV1

• Perform Kerberoasting

• Abuse a WordPress Plugin function for a Relay attack

Gaining Access to the Domain Controller

• Gather information to prepare client-side attacks

• Leverage client fingerprinting to obtain information

Module 25 - Trying Harder: The Labs

PWK Challenge Lab Overview

• Learn about the different kinds of Challenge Labs

• Obtain a high level overview of each scenario

• Understand how to treat the mock OSCP Challenge Labs

Challenge Lab Details

• Understand how to think about the concept of dependency

• Understand the lack of meaning inherent to IP address ordering

• Learn about the concept of “decoy” machines

• Learn how Routers and Network Address Translation affect the scenarios

• Understand how to treat the credentials and password attacks

Module 26 - The OSCP Exam Information

• Learn about the OSCP Certification Exam

About your OffSec instructors:

Nassereddine Abdelli

Nassereddine (Nasro), a Technical Trainer at OffSec, has a decade of professional information security experience in both the offensive and defensive fields. He ran his own online information security learning platform prior to joining OffSec and is always working on something infosec related in his free time.

Jon Michael Mancao

Jon started as a Software Engineer before entering the information security field. He loved investigating how things work and eventually dabbled in the inner workings of Operating Systems and Computer Architecture. There he discovered buffer overflows and started aiming for OSCP. He joined OffSec as a Student Mentor, where his experience in assisting and mentoring students was beneficial to his role as an OffSec Academy instructor.