OSWE Certification: Ultimate 2025 Guide to OffSec WEB-300

Published: October 15, 2025 | 5 min read

If you want a certification that proves you can read real web application code and turn subtle bugs into reliable exploits, the Offensive Security Web Expert (OSWE) certification is for you. Unlike scanner-heavy or checklist-style exams, OSWE tests whether you can dissect source code, chain multiple vulnerabilities, and script end-to-end attacks that work every time. In this guide, we’ll break down everything about the OSWE certification—from the WEB-300 course and exam format to preparation tips, pricing, and career impact—so you can plan your path with confidence.

What Is the OSWE and Why It Matters

The Offensive Security Web Expert (OSWE) is the capstone certification for practitioners who specialize in advanced web exploitation through code review. It’s tied to OffSec’s WEB-300: Advanced Web Attacks and Exploitation course. You pass the WEB-300 exam, you earn OSWE. Simple. But getting there takes real skill.

Here’s what makes OSWE different:

It’s a white-box exam. You will read and reason about source code to find logic flaws and deep vulnerabilities.
You must craft non-interactive, end-to-end exploit scripts for each target—no manual clicking to finish the chain.
You submit a professional, reproducible report that documents every step clearly enough for someone else to replicate.

Actionable takeaway:

From week one of studying, practice writing complete proof-of-concept scripts that run without human input. Treat every lab as a chance to automate the whole chain. Your exam success depends on it.

Where OSWE Fits Among OffSec Certs

OSWE sits alongside OSEP (evasion/red team) and OSED (exploit development) as one of the three advanced certifications in OffSec’s OSCE3 recognition pathway. OSCP is a great generalist foundation; OSWE is a specialist credential that proves deep web exploitation ability. Many organizations look for OSWE explicitly in job postings for application security and product security roles.

Actionable takeaway:

If you’re shaping a career in appsec or product security, OSWE is a strong differentiator. If you aim for OffSec’s OSCE3 status, OSWE is one of the three pillars to earn.

Exam Format, Scoring, and Deliverables

OSWE is a remote, proctored, hands-on exam that mirrors high-stakes, real-world assessments. You’ll connect to an exam network via VPN and work on a small number of targets.

Key facts:

Timebox: 47 hours 45 minutes of exam time, plus 24 hours to submit your report.
Environment: Kali + OpenVPN to a private exam network; strict proctoring requirements apply (webcam, OS/hardware, network).
Scoring: Up to 100 points total; 85 required to pass. Partial credit may be available.
Deliverables: For each target, submit a single, non-interactive exploit script that retrieves proof(s). Also deliver a thorough, reproducible report: commands, output, relevant code, and all steps.
Restrictions: No mass scanners or source code analyzers, no automatic exploiters, and no AI chatbots/LLMs during the exam. The guide’s allowed/disallowed list governs.

Actionable takeaway:

Rehearse the entire exam flow at least once: 36–40 hours of exploitation under tool limits, followed by a 24-hour reporting window. This simulation will surface time-management and documentation weaknesses before exam day.

Eligibility and Recommended Background

There are no formal prerequisites. OffSec recommends comfort in at least one programming language, Linux fluency, scripting (Python/Perl/PHP/Bash), using web proxies (e.g., Burp), and familiarity with common web vulns. These expectations align with what the exam really tests.

Actionable takeaway:

Choose a primary stack to specialize in for prep—PHP, .NET, or Java—and get fast at reading, decompiling, and debugging that stack. You’ll learn faster when your tooling and language basics are second nature.

What OSWE Tests: The Skills and Topics

OSWE goes beyond simple injection or XSS. The exam expects you to understand software behavior and framework quirks well enough to chain nuanced bugs into complete attacks. OffSec highlights skill areas such as:

Blind SQL injection and data exfiltration paths
Type juggling and “magic hashes” in weak comparisons
Bypassing upload, extension, and regex filters
Chained CSRF/XSS leading to credential theft or code execution
PostgreSQL LO/UDF techniques
.NET debugging and deserialization
Source code review across PHP, .NET, Java, JavaScript, Python contexts

Actionable takeaway:

Build a personal “attack patterns” notebook that maps each skill (e.g., type juggling) to 2–3 concrete code signatures or framework antipatterns you can quickly spot in source.

Study Resources That Work

Your best starting point is OffSec’s own WEB-300 content and labs. But to deepen and broaden your skills, include:

PortSwigger Web Security Academy for hands-on practice with modern web bugs (API attacks, request smuggling, cache poisoning, SSRF). Its labs complement WEB-300’s depth with breadth.
OWASP Web Security Testing Guide (WSTG) to organize your methodology across authentication, session, access control, business logic, client-side testing, etc.

Actionable takeaway:

Pair every PortSwigger lab with a “non-interactive” PoC script where feasible. This habit will pay off on exam day when you must automate end-to-end proof retrieval.

A 10–12 Week OSWE Study Plan

Use this as a template—adjust based on your schedule and background.

Weeks 1–2: Stack setup and fundamentals

Pick a primary stack (PHP/.NET/Java). Install debuggers and decompilers (e.g., dnSpy/ILSpy for .NET, JD-GUI/JD-IntelliJ for Java).
Refresh language internals: serialization/deserialization APIs, file handling, authentication flows, template engines, dependency injections.
Do targeted PortSwigger labs aligned to your stack; take notes on antipatterns and payload variations.

Week 3: WEB-300 orientation and first chains

Work through WEB-300 modules with the mindset: “How do I turn this into a single non-interactive exploit script?”
Create a base exploit template per language (argument parsing, HTTP client, session cookies, CSRF token extraction, file upload, error handling).

Weeks 4–6: Build exploit muscle memory

Pick 2–3 public advisories or blogged vulns per week and implement fully automated PoCs that retrieve a “proof artifact.”
After each, write a concise, reproducible report. Practice including code snippets, I/O, and screenshots where appropriate.

Weeks 7–8: Deep dives into tricky areas

Type juggling and weak comparisons; regex/upload bypasses; .NET/Java deserialization; chained CSRF/XSS; database file I/O paths.
For each topic, implement at least one end-to-end PoC and a short write-up.

Week 9: Mini sprints

Two separate 12–16 hour sprints with exam-like constraints (no disallowed tools; strict automation; comprehensive notes).

Week 10: Long sprint + reporting

One 36–40 hour rehearsal; submit a full report within 24 hours. Review against OSWE guide expectations and identify gaps.

Weeks 11–12: Polish and logistics

Tighten your exploit templates, reporting checklist, and code comments.
Run a proctoring tech check; validate webcam, bandwidth, VM stability, and screen-sharing behavior. Prepare a backup connection plan.

Actionable takeaway:

Treat reports as products: aim for a teammate to reproduce your steps without asking you questions. That standard is what OSWE grading expects.

Tooling, Environment, and Proctoring Setup

OSWE is proctored and remotely delivered. Before exam day:

Validate your hardware, operating system compatibility, webcam, and internet bandwidth.
Ensure your virtualization stack is stable with screen sharing.
Confirm your VPN client and Kali install work cleanly with the exam setup.
Conduct a dry run of your workspace: dual monitors if allowed, font sizes, terminal layout, note-taking template, and timestamped screenshot workflow.

Actionable takeaway:

Run a 60–90 minute “proctoring rehearsal” a week before your exam: share screens, move windows, and simulate common actions to uncover any UI or connectivity snags early.

Policies You Should Know: Retakes, Scheduling, and Validity

Retakes and scheduling

OffSec enforces retake cooling-off periods after failed attempts (4 weeks after the first failure, 8 weeks after the second, 12 weeks after the third+). Retake vouchers usually carry a 120-day validity. Plan accordingly.
Manage scheduling through OffSec’s exam system (“Classic Flow” process). Don’t wait until the last week to book your slot.

Validity

As of October 2025, OSWE does not expire. OffSec’s expiring model applies to certain newer credentials like OSCP+, OSCC-SEC, OSCC-SJD, OSTH, and OSIR, which rely on renewal and AMF/CPE programs.

Actionable takeaway:

If you hold expiring OffSec certs (e.g., OSCP+), earning another qualifying certification can help with renewal; OSWE itself is non-expiring but can complement broader credential planning. Verify your situation in OffSec’s renewal docs.

Pricing and Access (as displayed in OffSec’s portal)

Individual learners typically choose between:

WEB-300 Course & Certification Exam Bundle (90 days access, 1 attempt): $1,749
Learn One (1 year, includes WEB‑300 + 2 exam attempts, plus fundamentals and other benefits): $2,749/year
Learn Unlimited: OffSec support examples list $6,099/year; confirm current price in your cart or via sales (org purchases vary).

Notes:

Subscriptions are generally non-refundable; bundles have specific policies. Review OffSec’s terms before purchase.

Actionable takeaway:

If you want more runway and a safety net, Learn One’s extra attempt and longer access can be worth it. If you’re focused and time-bound, the 90-day bundle may fit better—book and back-plan your study calendar to the day.

High-Impact Practice Themes

Focus on problems scanners miss and that require code insight:

Authentication and authorization edge cases: inconsistent comparisons, role checks in the wrong layer, signed token misuse.
File and upload flows: content-type, regex, and extension filters; storage and path handling; image processing quirks.
Serialization/deserialization: language-specific pitfalls (.NET BinaryFormatter, Java deserialization chains).
Database leverage: PostgreSQL large objects and UDFs that open paths to file system or code execution.

Actionable takeaway:

For each theme, create a “quickstart” snippet in your exploit template (e.g., for CSRF token scraping, multi-part file upload, boundary conditions for loose comparisons). Having these snippets ready saves hours during the exam.

Writing the OSWE-Grade Report

Your report is as important as your shell. To earn full points:

Make it reproducible end-to-end: commands, parameters, expected outputs, screenshots where appropriate.
Include the full exploit source per target and usage instructions.
Avoid assumptions: if a step depends on state, document how to set that state.
Use consistent formatting and headings; keep it readable and concise.

Actionable takeaway:

Build a report template now. Include sections for Summary, Environment, Steps to Reproduce, Exploit Code, Proofs, and Remediation Suggestions (optional but professional). Fill it during practice so it’s second nature on exam day.

Career Value and How to Showcase OSWE

Employers love candidates who can move beyond “scanner says high” to “here’s the code path, here’s the exploit, here’s how to fix it.” OSWE signals exactly that. It shows you can read real apps, find non-trivial, multi-stage issues, and turn them into reliable PoCs—skills in high demand across appsec and product security roles. Job postings frequently list OSWE as preferred or required, often at six-figure salary ranges in the U.S. (ranges depend on region and experience).

Actionable takeaway:

Publish redacted practice write-ups (not exam content) demonstrating your methodology and automation. Pair OSWE on your résumé with 1–2 public PoCs to show your depth.

Common Pitfalls (and How to Avoid Them)

Over-reliance on interactive steps. The exam requires non-interactive exploit scripts; practice that way from the start.
Neglecting the report. Incomplete or ambiguous documentation can cost points even with a working exploit.
Using disallowed tools or AI. Learn the rules and stick to them; violations can nullify your attempt.
Underestimating logistics. Proctoring or VPN hiccups can derail momentum; test everything in advance.

Actionable takeaway:

Add a “pre-exam checklist” to your calendar one week before test day: proctoring dry run, backup internet, templates ready, exploit boilerplates validated.

Putting It All Together: A Simple OSWE Roadmap

Decide your access path (90-day bundle vs. Learn One year). Book your exam date now to anchor your study plan.
Pick a primary stack and set up your debugging/decompiling workflow.
Work through WEB-300, augment with PortSwigger labs, and align everything to fully automated PoCs.
Do at least one multi-day rehearsal and a 24-hour report sprint to finish.
Confirm proctoring requirements and tooling restrictions; adjust your workflow accordingly.

FAQs

Q1: How long is the OSWE exam?
A1: 47 hours 45 minutes of hands-on exam time plus a 24-hour report window.

Q2: Is OSWE proctored and what are the tech requirements?
A2: Yes, OSWE is proctored. You’ll need compatible hardware/OS, a working webcam, stable bandwidth, and a suitable virtualization setup. Test these ahead of time.

Q3: What’s the passing score and how is it calculated?
A3: You need 85 points out of 100. Points come from successfully exploiting targets and submitting required deliverables according to the guide.

Q4: What must I submit to pass?
A4: For each target, a single non-interactive exploit script that retrieves proofs, plus a professional, reproducible report detailing steps, commands, outputs, and code.

Q5: Are there tool restrictions or AI usage rules?
A5: Yes—mass scanners, source analyzers, automated exploiters, and AI chatbots/LLMs are not allowed during the exam. Follow the official guide.

Q6: Does OSWE expire?
A6: No. As of October 2025, OSWE does not expire. OffSec’s expiring model applies to certain other credentials like OSCP+.

Q7: How much does it cost?
A7: The WEB-300 Course & Cert Exam Bundle shows $1,749 in the OffSec checkout; Learn One shows $2,749/year. Learn Unlimited pricing varies—OffSec support examples reference $6,099/year. Always confirm current prices in your cart.

Conclusion:
If you want to prove you can do more than run scanners—that you can read code, reason about complex systems, and produce reliable exploit chains—the OSWE certification is worth your time. Plan your study, practice full non-interactive PoCs, rehearse the exam/report timing, and lock down your proctoring setup in advance. You’ll walk into exam day with confidence and walk out with a credential employers respect.

🌟 About FlashGenius

FlashGenius is your all-in-one AI-powered exam prep platform for mastering IT, cloud, AI, cybersecurity, and healthcare certifications. Whether you’re just starting out or leveling up your career, FlashGenius helps you prepare faster, smarter, and more confidently through:

Learning Path: Personalized, step-by-step study plans tailored to your certification goals.
Domain & Mixed Practice: Targeted question sets to sharpen your understanding across all exam domains.
Exam Simulation: Real exam-like tests that mirror actual certification conditions.
Flashcards & Smart Review: Reinforce weak areas and retain key concepts effortlessly.
Common Mistakes: Learn from thousands of users’ past errors to avoid common pitfalls.
Pomodoro Timer & Study Tools: Stay focused and productive throughout your study sessions.

From CompTIA and Microsoft to AWS, GIAC, NVIDIA, and Databricks, FlashGenius covers today’s most in-demand certifications with AI-guided learning, gamified challenges, and multilingual support — making exam prep engaging and effective.

👉 Start your free practice today at FlashGenius.net and accelerate your journey to certification success!