🎭 Rogue → Penetration Tester
“The best way to understand defenses is to break them. Ethically. With permission. And a signed contract.”
Your Role in the Party
You’re the person organizations hire to think like an attacker. While blue teamers build walls, you find the cracks—before actual adversaries do. Your job is to break into systems, networks, and applications, then explain exactly how you did it so defenders can fix it.
Penetration testing is controlled chaos. You have a scope, a timeline, and rules of engagement, but within those boundaries, creativity reigns. Every engagement is a puzzle: reconnaissance, enumeration, exploitation, privilege escalation, lateral movement, and finally—the report that makes it all matter.
This role rewards hands-on learners. If you learn by doing, by breaking things and seeing what happens, by iterating through trial and error until something clicks—you’re built for this work.
📊 Your Stat Spread
| Stat | Score | What It Means for You |
|---|---|---|
| STR | ⭐⭐⭐⭐⭐ | Learn by breaking things. Hands-on execution is your primary mode. |
| DEX | ⭐⭐⭐⭐⭐ | Rapid pivoting during engagements. Adapt when Plan A fails. |
| INT | ⭐⭐⭐ | Enough theory to be effective. You know why attacks work, not just how. |
| WIS | ⭐⭐⭐ | Spot vulnerabilities intuitively. Pattern recognition guides exploitation. |
| CHA | ⭐⭐⭐ | Report writing and client communication. Your findings need to be understood. |
| CON | ⭐⭐ | Sprint-based work. Intense engagements followed by report writing, then reset. |
🎭 Neurodivergent Advantages
Your traits are class features, not bugs:
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Rapid Context-Switching (DEX): ADHD’s ability to pivot quickly is exactly what penetration testing demands. When one attack vector fails, you’re already trying the next. Your brain doesn’t get stuck—it moves.
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Learn by Doing (STR): If reading documentation makes your eyes glaze over but running the exploit makes it click—that’s pentesting. This field rewards kinesthetic learners who need to do things to understand them.
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Novelty-Seeking as Strategy: Every engagement is different. New networks, new applications, new puzzles. ADHD’s need for novelty is met by a career where repetition is the exception.
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Hyperfocus During Engagements: When you find a promising attack path, hyperfocus becomes your weapon. Four hours disappear while you chase a shell.
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Unconventional Thinking: The weird mental connections ADHD and autistic brains make? Those become your most creative attack vectors. You see paths others miss because your brain doesn’t follow the obvious route.
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Pattern Recognition: Autistic attention to detail catches the misconfiguration, the exposed credential, the overlooked service that becomes your entry point.
🗺️ Career Path
IT Support/Security Analyst → Junior Pentester → Pentester → Senior Pentester → Red Team Lead
↓ ↓ ↓ ↓
(Foundation) (Learn the (Specialize) (Lead teams or
craft) pivot to
consulting)Common Rogue Multiclasses:
- Rogue/Warlock: Pentester → Purple Team (attack and defend, bridge the gap)
- Rogue/Sorcerer: Pentester → Security Researcher (find 0-days, not just exploit known vulns)
- Rogue/Artificer: Pentester → Red Team Tool Developer (build custom implants and frameworks)
📜 Certification Pathway
Level 1-5: Foundation (0-2 years)
| Certification | Org | Type | Cost | Why It Fits |
|---|---|---|---|---|
| CompTIA Security+ | CompTIA | Multiple Choice | ~$425 | Foundation. Understand security concepts before you break them. |
| CompTIA PenTest+ | CompTIA | Multiple Choice + Performance | ~$404 | Entry-level pentest cert. Good stepping stone, less respected than practical certs. |
| eJPT (eLearnSecurity Junior Penetration Tester) | INE Security | Practical (48 hrs) | ~$200 (includes free training) | Entry-level practical cert. Browser-based exam, real pentesting tasks. Free retake included. |
Neurodivergent Note: Skip to eJPT if multiple-choice exams destroy your soul. It’s practical, affordable, and respected as an entry point. The 48-hour window accommodates different working styles.
Level 6-10: Specialization (2-5 years)
| Certification | Org | Type | Cost | Why It Fits |
|---|---|---|---|---|
| PNPT (Practical Network Penetration Tester) | TCM Security | Practical (5 days) + Report + Debrief | ~$399 (with training) | Most realistic exam on the market. Full scope-to-report workflow. Live debrief with senior pentesters. |
| OSCP+ (Offensive Security Certified Professional) | OffSec | Practical (24 hrs) | ~$1,749 (course + labs + exam) | THE industry standard. “Try Harder” methodology. Now requires renewal every 3 years. |
| GPEN (GIAC Penetration Tester) | SANS/GIAC | Multiple Choice (3 hrs) | ~$999 (exam) + ~$8,000+ (SEC560) | DoD/government recognized. SEC560 course is excellent but expensive. |
| CPTS (Certified Penetration Testing Specialist) | Hack The Box | Practical | ~$490 (exam only) | HTB’s practical cert. Challenging, respected, more affordable than OSCP. |
Neurodivergent Note: PNPT is the most ND-friendly mid-tier cert—5 days to work at your own pace, realistic workflow, and the debrief is actually helpful (not a gotcha). OSCP is a rite of passage but the 24-hour pressure cooker isn’t for everyone. CPTS is a solid alternative if HTB’s style resonates.
Level 11-15: Advanced (5-8 years)
| Certification | Org | Type | Cost | Why It Fits |
|---|---|---|---|---|
| OSEP (Offensive Security Experienced Penetration Tester) | OffSec | Practical (48 hrs) | ~$1,749 (course + labs + exam) | Advanced pentesting. Evasion, custom payloads, mature environments. |
| OSWE (Offensive Security Web Expert) | OffSec | Practical (48 hrs) | ~$1,749 | Web application focus. Source code review, exploit development. |
| CRTO (Certified Red Team Operator) | Zero-Point Security | Practical | ~$449 (course + exam) | Cobalt Strike and red team operations. Excellent value. |
| GXPN (GIAC Exploit Researcher and Advanced Penetration Tester) | SANS/GIAC | Multiple Choice | ~$999 (exam) + course | Advanced exploitation. Memory corruption, custom exploits. |
Neurodivergent Note: CRTO is exceptional value and Daniel Duggan’s teaching style is clear and methodical. The 48-hour windows on OSEP/OSWE are more forgiving than OSCP’s 24.
Level 16-20: Mastery (8+ years)
| Certification | Org | Type | Cost | Why It Fits |
|---|---|---|---|---|
| OSEE (Offensive Security Exploitation Expert) | OffSec | Practical (72 hrs) | ~$1,749+ | The hardest offensive cert. Windows kernel exploitation. Very few hold this. |
| OSCE3 | OffSec | Trilogy Completion | Pass OSEP + OSWE + OSED | Proves mastery across web, network, and exploit development. |
| GREM (GIAC Reverse Engineering Malware) | SANS/GIAC | Practical | ~$999 (exam) + course | Understand malware to write better implants and evade detection. |
🛠️ Your Toolkit
Primary Weapons
| Tool | Type | What It Does | Link |
|---|---|---|---|
| Burp Suite Professional | Web App Testing | Industry standard for web application pentesting. Intercept, modify, exploit. | portswigger.net |
| Metasploit Framework | Exploitation | World’s most used pentest framework. Exploit development, post-exploitation, pivoting. | metasploit.com |
| Cobalt Strike | Adversary Simulation | Commercial C2 framework. Red team standard. ~$3,540/year license. | cobaltstrike.com |
| Kali Linux | Operating System | Purpose-built for pentesting. Pre-loaded with tools. | kali.org |
Reconnaissance & Enumeration
| Tool | Purpose | Link |
|---|---|---|
| Nmap | Network scanning and service enumeration. The first tool you run. | nmap.org |
| Rustscan | Fast port scanner. Feeds results to Nmap. | GitHub |
| Nuclei | Template-based vulnerability scanner. Huge community template library. | GitHub |
| ffuf | Web fuzzing. Directory brute-forcing, parameter discovery. | GitHub |
| Amass | Attack surface mapping. Subdomain enumeration at scale. | GitHub |
Active Directory & Internal Networks
| Tool | Purpose | Link |
|---|---|---|
| BloodHound | AD attack path visualization. Find paths to Domain Admin. | GitHub |
| Impacket | Python library for network protocols. Secretsdump, psexec, wmiexec, and more. | GitHub |
| CrackMapExec / NetExec | Swiss army knife for AD pentesting. Spray, execute, pwn. | GitHub |
| Mimikatz | Credential extraction. The tool defenders fear. | GitHub |
| Responder | LLMNR/NBT-NS poisoning. Capture hashes on internal networks. | GitHub |
Web Application Testing
| Tool | Purpose | Link |
|---|---|---|
| OWASP ZAP | Free web app scanner. Burp alternative. | zaproxy.org |
| SQLMap | Automated SQL injection detection and exploitation. | sqlmap.org |
| Caido | Modern web security testing. Burp alternative with better UX. | caido.io |
| Postman / Insomnia | API testing. Understand APIs before attacking them. | postman.com |
C2 Frameworks (Cobalt Strike Alternatives)
| Tool | Purpose | Link |
|---|---|---|
| Sliver | Open-source C2 by BishopFox. Growing rapidly. | GitHub |
| Havoc | Modern, open-source C2 framework. | GitHub |
| Mythic | Collaborative C2 with web UI. Multi-platform agents. | GitHub |
| Empire | PowerShell/Python post-exploitation. Modular C2. | GitHub |
Fun Tools from Awesome Lists
Source: awesome-pentest
| Tool | What It Does |
|---|---|
| Ligolo-ng | Tunneling/pivoting made easy. Establish tunnels without needing SOCKS. |
| Villain | C2 framework with multi-session handling and auto-completion. |
| Kerbrute | Kerberos brute-forcing and user enumeration. |
| LaZagne | Credential recovery from numerous applications. |
| Evil-WinRM | Ultimate WinRM shell for pentesting. |
📚 Learning Resources
Free Resources
YouTube Channels:
- IppSec - HackTheBox walkthrough king. Learn methodology by watching.
- John Hammond - CTF walkthroughs, malware analysis, great explanations.
- The Cyber Mentor - TCM Security’s free content. PNPT creator.
- LiveOverflow - Deep technical exploits explained well.
- STÖK - Bug bounty content with good energy.
Practice Platforms:
- Hack The Box - Industry standard. Free tier available.
- TryHackMe - More guided, beginner-friendly. Excellent paths.
- PortSwigger Web Security Academy - Free web app hacking training from Burp creators.
- PentesterLab - Progressive web security exercises.
- VulnHub - Downloadable vulnerable VMs. Build your own lab.
- DVWA - Damn Vulnerable Web Application. Classic practice target.
CTF Practice:
- PicoCTF - CMU’s beginner CTF. Always available.
- OverTheWire - Wargames for learning Linux and security basics.
- CTFtime - Calendar of live CTF competitions.
Books for Rogues
| Book | Author | Why Read It |
|---|---|---|
| The Hacker Playbook 3 | Peter Kim | Practical pentesting methodology. Step-by-step like a real engagement. |
| Penetration Testing | Georgia Weidman | Comprehensive intro. Covers methodology, tools, and techniques. |
| Red Team Development and Operations | Joe Vest & James Tubberville | How red teams actually operate. Beyond individual pentesting. |
| Web Application Hacker’s Handbook | Stuttard & Pinto | Bible of web app hacking. Pair with PortSwigger Academy. |
| Black Hat Python | Justin Seitz | Python for pentesters. Automate your attacks. |
| Attacking Network Protocols | James Forshaw | Deep protocol analysis. Understand what you’re exploiting. |
Podcasts
| Podcast | Why Listen |
|---|---|
| Darknet Diaries | Real stories of hacking. Motivation fuel. |
| Risky Business | Weekly security news with technical depth. |
| Hacking Humans | Social engineering focus. CyberWire production. |
| Malicious Life | Historical hacking stories. Cybereason production. |
| The Cyber Ranch | Red team focused discussions. |
🎓 SANS Courses for Rogues
| Course | Cert | Focus | Best For |
|---|---|---|---|
| SEC560: Network Penetration Testing | GPEN | Core pentesting methodology | Foundation |
| SEC542: Web App Penetration Testing | GWAPT | Web application attacks | Web-focused pentesters |
| SEC660: Advanced Penetration Testing | GXPN | Exploit writing, advanced techniques | Moving beyond basics |
| SEC565: Red Team Operations | GRTP | Full red team methodology | Red team career track |
| SEC588: Cloud Penetration Testing | GCPN | AWS, Azure, GCP pentesting | Cloud-focused roles |
🏆 Building Your Magic Items
Early Career Achievements:
- Root your first HackTheBox machine
- Complete TryHackMe “Jr Penetration Tester” path
- Build a home lab with vulnerable VMs
- Earn eJPT certification
- Write your first professional-style pentest report
Mid-Career Achievements:
- Conduct your first professional engagement
- Earn OSCP or PNPT certification
- Find a bug in a bug bounty program
- Develop a custom tool that helps your workflow
- Present findings to a client executive
Senior Achievements:
- Lead a red team engagement
- Earn OSEP, OSWE, or CRTO
- Speak at a security conference (BSides, DEF CON village, etc.)
- Mentor junior pentesters
- Contribute to an open-source security tool
🧭 Multiclassing Guide
Adding Warlock Levels (Purple Team)
Bridge offense and defense:
- Learn detection engineering—understand what blue teams see
- Study MITRE ATT&CK from both sides
- Practice with Atomic Red Team and Caldera
- SANS SEC599: Defeating Advanced Adversaries
“I don’t just break in—I help defenders detect the techniques I use.”
Adding Sorcerer Levels (Security Research)
Move from exploiting known vulns to finding new ones:
- Learn fuzzing with AFL++ and LibFuzzer
- Study vulnerability research methodology
- Practice on VulnHub and self-hosted targets
- Read CVE writeups and reproduce exploits
“I don’t just run other people’s exploits—I find the vulnerabilities myself.”
Adding Artificer Levels (Tool Development)
Build custom implants and frameworks:
- Master Python, then learn C/C++ or Rust
- Study malware development (for red team purposes)
- Contribute to open-source C2 frameworks
- SANS SEC760: Advanced Exploit Development
“I don’t just use Cobalt Strike—I build tools that do what off-the-shelf can’t.”
💡 Neurodivergent Learning Strategies
For ADHD:
- Pentesting’s variety is your friend—each engagement is different
- Use CTFs and HackTheBox as gamified learning (dopamine hits from pwning)
- Time-boxed engagements provide external structure
- Let rabbit holes happen during practice; learn to timebox during client work
- The “try harder” mentality can feel natural when interest is captured
For Autism:
- Build systematic methodologies and checklists (enumeration scripts, report templates)
- Deep-dive on specific attack types (AD, web apps, cloud) as special interests
- Technical documentation and report writing leverage systematic communication
- Predictable engagement phases provide structure within chaos
- Pattern recognition helps identify vulnerabilities others miss
For Both:
- Hands-on learning is the only learning that sticks—embrace it
- Your “weird” approaches become creative attack vectors
- Hyperfocus during engagements is a competitive advantage
- Build tools and automations that match how your brain works
- The community (CTF teams, Discord servers) often skews ND—you’ll find your people
🎯 Not Sure If You’re a Rogue?
Take the Character Creation Quiz to discover your cybersecurity class and get personalized recommendations!
📖 Continue Your Journey
- View All Classes
- Red Team: Barbarian - If incident response calls to you
- Purple Team: Warlock - If you want to bridge offense and defense
- Red Team: Sorcerer - If finding new vulnerabilities interests you
“Every network has holes. Your job is to find them first, document them clearly, and help close them before someone else gets there.”