OffSec Experienced Penetration Tester (OSEP, PEN-300) Practice Test
Prepare for the OffSec OSEP exam with free practice tests built around the real hands-on PEN-300 certification. Each test includes 20 questions with a proportional timer of about 5 hours to help you build the endurance, evasion mindset, lateral movement workflow, and reporting discipline needed for advanced enterprise penetration testing.
Mixed Set — OffSec Experienced Penetration Tester (OSEP, PEN-300) Practice Tests
These mixed sets pull questions from the major PEN-300 learning areas, including code execution, evasion, credential theft, Active Directory abuse, pivoting, post-exploitation, and reporting. They are designed to reflect how the real OSEP expects you to combine tradecraft, tooling, and methodology instead of solving isolated theory questions.
Domain Wise — OffSec Experienced Penetration Tester (OSEP, PEN-300) Mock Tests
Use these targeted topic-wise tests to focus on one PEN-300 skill area at a time. Each mock test contains 20 questions built around a single advanced offensive topic so you can sharpen weak areas before returning to mixed practice.
About the OffSec Experienced Penetration Tester (OSEP) Certification Exam
Everything you need to know about PEN-300, the OSEP exam, eligibility expectations, and why advanced evasion and enterprise compromise skills matter for modern penetration testing.
What Is the OSEP?
The OffSec Experienced Penetration Tester (OSEP) is the certification aligned to PEN-300, OffSec’s Evasion Techniques and Breaching Defenses course. OffSec describes PEN-300 as an advanced penetration testing course for experienced offensive security practitioners, focused on breaching and operating within hardened targets and mature organizations with established security programs. :contentReference[oaicite:1]{index=1}
OSEP is best suited for penetration testers, red teamers, adversary emulation practitioners, internal security consultants, and offensive security professionals who want stronger tradecraft for bypassing defenses, moving laterally, and operating beyond entry-level pentesting techniques. Related information security analyst roles in the United States had a median annual wage of $124,910 in May 2024. :contentReference[oaicite:2]{index=2}
Exam Format (2026)
Testing method: Practical, proctored enterprise penetration testing exam. :contentReference[oaicite:3]{index=3}
Exam/course code: PEN-300 leading to the OSEP certification. :contentReference[oaicite:4]{index=4}
Exam environment: A live network simulation in a private VPN. :contentReference[oaicite:5]{index=5}
Duration: 47 hours 45 minutes for the exam, plus 24 hours to upload the required report. :contentReference[oaicite:6]{index=6}
Question style: Practical exploitation objectives and reporting requirements rather than multiple-choice questions. :contentReference[oaicite:7]{index=7}
Passing score: At least 75 points out of 100. :contentReference[oaicite:8]{index=8}
Resources allowed: Open book, with OffSec’s current restrictions on prohibited resources still applying. :contentReference[oaicite:9]{index=9}
Training price: Course + Cert Bundle is listed at $1,749 with 90 days of access and 1 exam attempt, while Learn One is $2,749 per year with 1 year of access and 2 exam attempts. :contentReference[oaicite:10]{index=10}
Eligibility Requirements
Formal prerequisite: None listed publicly for sitting the exam. :contentReference[oaicite:11]{index=11}
Recommended background: OffSec says PEN-300 learners should already have a solid understanding of Linux, networking, Bash or Python, and penetration testing fundamentals. :contentReference[oaicite:12]{index=12}
Report requirement: You must submit a professional technical report after the exam. :contentReference[oaicite:13]{index=13}
Retake policy: OffSec says all exams have a cooling-off period. Its current policy is 4 weeks after a first failed exam, 8 weeks after a second failed exam, and 12 weeks after a third failed exam onward. :contentReference[oaicite:14]{index=14}
Exam validity model: Exam-attempt validity depends on the OffSec product purchased. :contentReference[oaicite:15]{index=15}
OSEP Objective Weights — PEN-300 Practice Mapping
OffSec publicly explains the PEN-300 course scope and the OSEP exam format, but it does not publish a public percentage-weight table for the practical objectives on the surfaced official pages. Because this page uses 12 domain-wise tests, the table below uses an even practice mapping across those 12 topic groups so mixed sets remain balanced and predictable. :contentReference[oaicite:16]{index=16}
| Objective | Topic | Practice Weight |
|---|---|---|
| D1 | Operating System and Programming Theory | 8.3% |
| D2 | Client-Side Code Execution With Office | 8.3% |
| D3 | Customizing Code Execution | 8.3% |
| D4 | Antivirus Evasion | 8.3% |
| D5 | Application Whitelisting Bypass | 8.3% |
| D6 | Credential Theft | 8.3% |
| D7 | Active Directory Enumeration and Attacks | 8.3% |
| D8 | Pivoting, Tunneling, and Lateral Movement | 8.3% |
| D9 | Microsoft SQL Server Attacks | 8.3% |
| D10 | Linux Post-Exploitation | 8.3% |
| D11 | Windows Post-Exploitation | 8.3% |
| D12 | Reporting | 8.3% |
How Our Practice Tests Are Designed
Built around the official PEN-300 scope — OffSec describes PEN-300 as an advanced course about evasion techniques and breaching defenses, so these practice tests emphasize enterprise tradecraft, defense bypass, pivoting, and post-exploitation rather than generic pentest trivia. :contentReference[oaicite:17]{index=17}
Timer matched to the real exam pace — The live OSEP exam gives you 47 hours and 45 minutes for a long-form practical assessment. Each 20-question practice set is timed at about 5 hours to build sustained focus and realistic operational pacing. This timing is an inference based on the official exam duration and practical format. :contentReference[oaicite:18]{index=18}
Enterprise attacker mindset — The real exam expects you to breach hardened targets, move through a network, and document the full attack path, so these practice sets reward reasoning about execution, evasion, credential access, lateral movement, and reporting quality. :contentReference[oaicite:19]{index=19}
Reporting matters — Because OffSec requires a post-exam report upload, the question style reinforces disciplined note-taking, evidence capture, and clear explanation of how each compromise step was achieved. :contentReference[oaicite:20]{index=20}
OSEP Exam Preparation Tips
Study Strategy
Strengthen your foundations first: OffSec recommends solid Linux, networking, scripting, and pentesting fundamentals before PEN-300, so weak basics will slow you down in advanced evasion work. :contentReference[oaicite:21]{index=21}
Practice operating in defended environments: PEN-300 is about getting code execution and maintaining progress when controls get in your way, so spend time understanding AV, application control, credential access, and enterprise segmentation.
Think in attack chains: Strong OSEP preparation comes from linking client-side delivery, evasion, credential access, AD abuse, pivoting, and post-exploitation into one coherent path instead of treating them as separate topics.
Test-Taking Strategy
Plan the long exam window: With 47 hours and 45 minutes plus 24 hours for report upload, decide in advance how you will pace analysis, exploitation, breaks, sleep, and final documentation. :contentReference[oaicite:22]{index=22}
Document while you work: Do not wait until the end to reconstruct your path. Capture screenshots, commands, credentials, and pivot details as soon as you validate them.
Use open-book access wisely: Since the exam is open book, organize your notes and references so you can quickly retrieve commands, OPSEC reminders, and workflow steps without losing momentum. :contentReference[oaicite:23]{index=23}
Frequently Asked Questions
Ready to Test Your OSEP Skills?
Start with a mixed set to measure your readiness, then use topic-wise tests to sharpen the exact enterprise attack skills you need for PEN-300.
Start OffSec OSEP Practice Test 1 →
