There are already plenty of write-ups from people who passed the OSWE certification, and a fair number of posts about CWEE as well. However, there are still not many direct comparisons between the two.

I recently passed CWEE and, having previously gone through OSWE, decided to share my perspective to help others understand which certification might be the better fit depending on their goals.

Overview

Let's start with a quick breakdown of both certifications.

The Advanced Web Attacks and Exploitation (AWAE / WEB-300) course and the Offensive Security Web Expert (OSWE) certification are offered by OffSec. At the time of writing, the price starts at $1749 and includes 90 days of lab access along with one exam attempt. The course focuses on web vulnerabilities and their exploitation, largely aligned with the OWASP Top 10.

OSWE is essentially a continuation of WEB-200 (Web Attacks with Kali Linux) and the OSWA certification. The exam cannot be purchased separately from the course, and a retake costs $249.

The Certified Web Exploitation Expert (CWEE) is offered by Hack The Box and is based on modules from the "Senior Web Penetration Tester" path. To become eligible for the exam, you must complete all required modules and obtain an exam voucher.

In my case, I purchased a 1-year Gold Subscription, which included an exam voucher and cost around €1276 (~$1470). This subscription also provides access to many other HTB Academy modules. The voucher includes two exam attempts, and a retake effectively means buying a new voucher (€300, excluding taxes), again with two attempts.

There are ways to optimize costs (monthly subscription + separate voucher), but the access model in HTB Academy can be somewhat confusing (tiers, job paths, cubes, etc.). In practice, it's not always obvious whether you'll get access to all required modules with that approach.

Course Content and Learning Experience

Both courses are well-designed and cover common web vulnerabilities such as SQL Injection, Command Injection, XSS, SSTI, SSRF, and more. They also place strong emphasis on source code analysis.

OSWE (AWAE)

From a depth and difficulty perspective, OSWE felt more demanding.

The course focuses heavily on:

  • Understanding application logic
  • Research and analysis
  • Building exploitation chains
  • Setting up and managing your own environment

It feels like you're expected to already have a solid foundation before starting — which makes sense given that WEB-200 is considered a prerequisite.

The course includes both guided labs and independent challenges, covering white-box, grey-box, and black-box approaches.

However, in my opinion, the course alone is not entirely sufficient to pass the exam.

Some areas require additional preparation:

  • Limited coverage of tools like ysoserial
  • Database-specific nuances (MySQL, PostgreSQL, MSSQL)
  • The need for cheat sheets and payload templates

You should also:

  • Practice writing full-chain exploits (e.g., in Python)
  • Prepare reusable scripts (requests, email handling, simple web servers)
  • Revisit lab machines and build detailed PoCs

Since AI is not allowed during the exam, your scripting skills and manual workflow matter a lot.

OSWE Exam Experience

Due to OffSec policy, I won't go into details about the exam content, but here are the key points:

  • Duration: 47 hours 45 minutes (~48 hours)
  • Additional 24 hours to submit the report
  • Proctored exam
  • Passing score: 85 points
  • Requires exploit scripts, not just flags

The requirements are quite high. Within a limited timeframe, you need to:

  • Identify vulnerabilities
  • Exploit them
  • Develop working PoC scripts
  • Write a detailed report

And all of this includes time for sleep, food, and rest.

The biggest challenge here is time pressure. If you get stuck on one target, it's easy to lose track of time, miss something small, and eventually fail due to poor time management rather than lack of knowledge.

Realistically, this exam should be planned for a weekend or taken with time off work.

CWEE Approach

CWEE takes a noticeably different approach.

Some vulnerabilities are presented in ways that may feel new, even for experienced testers. The course also references more basic modules, which can feel repetitive at times — but for some, this helps reinforce fundamentals.

Certain topics (like SSRF or SQL Injection) reappear across modules, sometimes in more advanced forms (e.g., second-order SQLi or deeper DB-specific cases). While this repetition may feel redundant, it does help build a stronger understanding over time.

Most labs are based on custom applications, although occasionally you'll encounter real-world CVEs.

A major advantage is the Pwnbox environment, which comes preconfigured with everything you need. Compared to OSWE, where environment setup and remote access could sometimes slow you down, this is a big plus.

CWEE Exam Experience

The CWEE exam format is very different:

  • Duration: 10 days from activation
  • 2 attempts per voucher
  • No proctoring
  • You can use any tools (including AI)
  • Requires a detailed report with PoCs
  • For white-box findings, you must suggest code-level fixes

This approach feels much closer to a real-world pentest.

You have:

  • Time to think and plan
  • Flexibility in tooling
  • Less psychological pressure

However, this does not make the exam easier.

One important point worth highlighting is that allowing AI and automation tools (such as SQLMap or fuzzing tools) does not devalue the exam.

In practice, many vulnerabilities require a deep understanding of application logic, data flow, and relationships between components. Automated tools alone are often not enough.

Moreover, over-reliance on AI can actually slow you down. It may suggest incorrect assumptions or lead you into a "rabbit hole", where you spend hours chasing irrelevant attack paths — especially in scenarios involving subtle logic flaws or multi-step exploit chains.

The exam still strongly rewards:

  • Manual analysis
  • Critical thinking
  • Understanding application behaviour
  • Building full exploitation chains

AI can help with small tasks, but it will not solve the exam for you.

Even with 10 days, the workload is significant. In my case, the final report ended up being larger than my OSWE report.

A key detail: if you fail your first attempt, you still must submit a report. Only then can you use your second attempt (within a 2-week window).

Final Thoughts

I wouldn't say one certification is strictly better than the other.

OSWE strengths:

  • Strong industry recognition
  • Deep focus on manual exploitation
  • Forces you to improve scripting and time management

CWEE strengths:

  • More realistic pentesting workflow
  • Flexible tooling (including AI)
  • Better lab environment
  • More forgiving timeline

In terms of content, both have pros and cons. Personally, I found CWEE more comprehensive overall, while OSWE is stronger in exploit development and working with real-world vulnerabilities.

What Should You Choose?

It depends on your background:

  • If you're already following the OffSec path → go for OSWE
  • If you're learning through Hack The Box → CWEE is a natural continuation
  • If you want strong industry recognition → OSWE
  • If you want a real-world pentesting experience → CWEE

Conclusion

In my opinion, both OSWE and CWEE are among the top certifications in web penetration testing today.

They serve slightly different purposes, but both are highly valuable depending on your goals.

Personally, I chose to do both — and I don't regret it.

Originally published at https://www.linkedin.com.