Hiring with a CTF Challenge

Aug 20, 2025

In the ever-evolving landscape of cybersecurity, finding and hiring skilled security engineers has become one of the most complex tasks for organizations. With cyber threats growing in sophistication and frequency, companies need professionals who aren’t just book-smart but passionate and curious about many things. Traditional recruitment methods: resumes, interviews, study cases often fall short in identifying true talent. Enter the Capture The Flag (CTF) challenge: a gamified, hands-on approach that’s transforming how we scout for infosec wizards. In this blog post, we’ll dive deep into why recruiting security engineers is so tricky, how an online CTF with eight targeted challenges can serve as the ultimate first barrier, and practical insights on implementing this strategy to build a good security team.

The Challenges of Recruiting Security Engineers

Let’s start with the basics: why is hiring security engineers such a headache? The field demands a unique blend of skills—technical skills: system administration, application security, cryptography, network security, and reverse engineering, combined with creative problem-solving and twisted mindset.

Traditional hiring pipelines exacerbate the problem. Resumes can be padded with buzzwords like “penetration testing” or “SIEM management,” but they don’t reveal how someone performs under pressure. Online meetings and whiteboard interviews might test theoretical knowledge, but they rarely simulate the the most importants aspects of a good security specialist. Moreover, unconscious biases in interviews can overlook diverse candidates from non-traditional backgrounds, such as self-taught specialist not comping from the traditional academic background.

By flipping the script and using practical, engaging challenges, companies can attract passive candidates who thrive on puzzles rather than job boards. A well-designed CTF not only filters out unqualified applicants but also excites top talent, turning recruitment into a viral event within the infosec community.

Why CTF Challenges Are the Perfect First Barrier

Capture The Flag competitions have long been a staple in cybersecurity conferences like DEF CON or Black Hat, where participants compete to “capture” digital flags by solving security puzzles. Adapting this to recruitment creates a merit-based gateway that weeds out pretenders while showcasing your company’s commitment to cutting-edge security. As the first barrier in your hiring process, an online CTF ensures that only those with genuine skills advance to interviews. It’s accessible—candidates can participate from anywhere—and scalable, handling hundreds of applicants without HR overload. Plus, it provides quantifiable metrics: time to solve, creative approaches, and persistence. For our hypothetical recruitment CTF, we’ll structure it around eight challenges, each progressively harder and targeting core security competencies. This isn’t just a random number; eight allows for breadth without overwhelming participants, typically taking 4-8 hours to complete for skilled candidates. The platform could be built on open-source tools like CTFd or hosted on AWS for ease. Let’s break down the eight challenges, including what they test, sample setups, and why they’re effective for screening.

Challenge 1: Web Basics – SQL Injection Hunt

Kick things off with a foundational web security puzzle. Participants are given a vulnerable web app (simulated on your CTF platform) where they must exploit an SQL injection flaw to retrieve a flag from a database. What it tests: Understanding of common web vulnerabilities (OWASP Top 10), basic SQL knowledge, and attention to detail. Why it’s a great opener: It’s accessible for junior engineers but reveals if someone has hands-on experience beyond theory. Top performers might use tools like SQLMap, showing tool proficiency. Tips for implementation: Use a Dockerized environment to reset instances per user, preventing cheating via shared exploits.

Challenge 2: Cryptography Crack – RSA Decryption

Move to crypto with a challenge where candidates decrypt a message encrypted with a weak RSA key (e.g., small modulus or common factors). What it tests: Mathematical foundations of cryptography, familiarity with tools like OpenSSL or Python’s cryptography library, and logical deduction. Why it’s effective: Security engineers often deal with encryption flaws in real life. This separates those who can apply number theory from rote learners. Pro tip: Provide hints for partial credit, like factoring tools, to gauge learning agility.

Challenge 3: Network Forensics – Packet Analysis

Supply a PCAP file from a simulated network capture containing hidden data or a flag embedded in traffic. What it tests: Proficiency with Wireshark or tcpdump, understanding of protocols (HTTP, DNS, etc.), and anomaly detection. Why it’s a barrier: Network security is core to infosec roles. Candidates who breeze through this demonstrate practical experience in incident response. Implementation note: Keep the file small to avoid frustrating downloads, and include red herrings to test thoroughness.

Challenge 4: Reverse Engineering – Binary Dissection

Present a simple binary executable (e.g., in C or Assembly) that, when reversed, reveals a flag via string analysis or function decompilation. What it tests: Skills in tools like IDA Pro, Ghidra, or radare2, and malware analysis basics. Why it’s crucial: Many threats involve reverse-engineering malware. This challenge filters for those with low-level programming chops. Enhancement: Add anti-debugging tricks for advanced solvers, revealing creative thinkers.

Challenge 5: Forensics Deep Dive – Memory Dump Mystery

A memory dump from a compromised system hides the flag, requiring volatility or similar tools to extract artifacts like process lists or hidden files. What it tests: Digital forensics expertise, volatility framework knowledge, and persistence in sifting through data. Why it’s a mid-point escalator: By now, casual applicants drop off, leaving those with real investigative skills. Best practice: Time-limit this to simulate real IR scenarios, tracking submission times.

Challenge 6: Exploitation – Buffer Overflow Exploit

Candidates craft an exploit for a buffer overflow vulnerability in a provided service, gaining shell access to grab the flag. What it tests: Exploit development, assembly language, and understanding of memory corruption. Why it’s high-bar: This is where true pentesters shine. It’s risky to implement, so use virtual machines and strict isolation. Safety first: Ensure challenges are ethical and don’t teach harmful real-world exploits without context.

Challenge 7: Cloud Security – AWS Misconfiguration Maze

Simulate an AWS environment with misconfigured S3 buckets, IAM roles, or EC2 instances hiding the flag. What it tests: Cloud-native security knowledge, AWS CLI proficiency, and awareness of common cloud pitfalls. Why it’s timely: With cloud adoption soaring, this targets modern security engineers versed in DevSecOps. Customization: Adapt for Azure or GCP if your stack differs, making it relevant to your org.

Challenge 8: Red Team Simulation – Multi-Stage Attack Chain

The finale: A chained challenge combining elements from prior ones, like pivoting from a web exploit to network traversal for the ultimate flag. What it tests: Holistic thinking, chaining vulnerabilities, and end-to-end attack simulation. Why it’s the closer: Only the elite complete this, providing a clear shortlist for interviews. Scoring twist: Award points for partial solves, creativity, and write-ups to assess communication skills.

Benefits and Potential Pitfalls of CTF Recruitment

Implementing a CTF as your first barrier yields massive upsides. It attracts talent from global hacker communities, reduces bias by focusing on skills, and generates buzz—imagine your CTF trending on Reddit’s r/netsec or Twitter’s infosec circles. Data from companies like Google (who use similar puzzles) shows higher retention rates for hires vetted this way, as they align with your culture. However, pitfalls exist. Not everyone excels in timed challenges; introverted geniuses might skip it. Accessibility issues, like requiring specific tools, could exclude underrepresented groups. Mitigate by offering flexible timing, clear instructions, and diverse difficulty levels. Cost-wise, building a CTF platform might run $1,000-$5,000 initially, but it’s reusable. Legal considerations: Ensure challenges comply with laws (no real exploits) and get participant consent for data usage. Best Practices for Launching Your CTF To make your CTF a success:

Promote widely: Post on LinkedIn, HackerOne, and cybersecurity forums. Offer swag for top solvers. Track metrics: Use leaderboards to identify standouts, but anonymize for privacy. Follow up: Invite qualifiers to interviews with feedback on their solutions—build rapport. Iterate: Analyze drop-off rates per challenge to refine future versions. Inclusivity: Provide beginner resources and accommodate disabilities (e.g., screen-reader friendly).

Conclusion: Level Up Your Hiring Game

In a world where security breaches can cost millions, settling for mediocre talent isn’t an option. By deploying an online CTF with eight meticulously crafted challenges as your recruitment’s first barrier, you’re not just hiring—you’re forging a team of elite defenders. This approach isn’t for every role, but for security engineers, it’s a game-changer. If you’re in HR or leading a security team, consider piloting a CTF today. Who knows? Your next hire might be the one who captures the flag and secures your future. What are your thoughts on CTF-based hiring? Share in the comments below—I’d love to hear success stories or tweaks!