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Penetration Testing Roadmap

Last updated: July 2026

A structured learning path from zero to junior penetration tester - topics, tools, labs, certifications, and hands-on guides.

Live roadmap:securitycipher.com/penetration-testing-roadmap

Quick start

  1. Read Intro.md for the recommended learning path and TL;DR
  2. Work through phases: Foundations → Web → Infrastructure → Specialize → Labs & certs
  3. Open any topic below for a short guide with tools, labs, and links
  4. See FAQ.md for career and cert questions

Learning path

PhaseFocusTime (part-time)
1. FoundationsLinux, networking, scripting, crypto basics4-6 weeks
2. Web securityHTTP, OWASP Top 10, Burp Suite, PortSwigger Academy6-8 weeks
3. InfrastructureAD basics, cloud, wireless, recon6-8 weeks
4. SpecializeWeb, cloud, mobile, API, or LLM trackOngoing
5. Prove itHTB, TryHackMe, certs (eJPT, Security+, OSCP)3-6 months

Full write-up: Intro.md

Content index

Getting started

Foundations

Core security

Web and application testing

Infrastructure and cloud

Emerging areas

Practice and credentials

Related Security Cipher resources

Certifications

CertGuide
CEHCEH.md
CISSPCISSP.md
CompTIA Security+CompTIA Security+.md
OSCPOSCP.md
OSWEOSWE.md
OSWPOSWP.md
eJPTeJPT.md
PNPTPNPT.md
CRTPCRTP.md
BTL1BTL1.md

Labs

PlatformGuide
Hack The BoxHackTheBox.md
TryHackMeTryHackMe.md
pwn.collegepwn.college.md
VulHubVulHub.md
Web Security AcademyWeb Security Academy.md
Root MeRoot Me.md
Altoro MutualAltoro Mutual.md

Contributing

Contributions are welcome. This repo is the source of truth for roadmap content.

  1. Fork the repo and create a branch
  2. Add or edit markdown under the right folder (one topic per file, clear headings, practical links)
  3. Open a pull request with a short description of what you added or fixed

Guidelines

  • Keep guides concise and actionable - labs, tools, and further reading where possible
  • Match the tone of existing topics (see Linux.md or SQL Injection.md)
  • Fix typos and broken links anytime - small PRs are fine
  • New topics: pick the closest folder from Content index above

All contributions are reviewed before merge. After merge, updates appear on the live roadmap on the next publish cycle.

Questions? Open a GitHub issue.

About

Complete Roadmap for Penetration Testing

securitycipher.com/penetration-testing-roadmap

Topics

bug-bountybugbountycybersecurityethical-hackinginfosecowasppenetration-testingpentestingroadmapsecuritysecurity-toolssecuritycipherweb-security

Resources

Readme
Activity

Stars

310 stars

Watchers

9 watching

Forks

53 forks
Report repository

Used by

Contributors

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GitHub - securitycipher/penetration-testing-roadmap: Complete Roadmap for Penetration Testing · GitHub
Skip to content
BranchesTags
Repository files navigation
Penetration Testing Roadmap
Last updated: July 2026
A structured learning path from zero to junior penetration tester - topics, tools, labs, certifications, and hands-on guides.
Live roadmap:securitycipher.com/penetration-testing-roadmap
Quick start
  1. Read Intro.md for the recommended learning path and TL;DR
  2. Work through phases: Foundations → Web → Infrastructure → Specialize → Labs & certs
  3. Open any topic below for a short guide with tools, labs, and links
  4. See FAQ.md for career and cert questions
Learning path
PhaseFocusTime (part-time)
1. FoundationsLinux, networking, scripting, crypto basics4-6 weeks
2. Web securityHTTP, OWASP Top 10, Burp Suite, PortSwigger Academy6-8 weeks
3. InfrastructureAD basics, cloud, wireless, recon6-8 weeks
4. SpecializeWeb, cloud, mobile, API, or LLM trackOngoing
5. Prove itHTB, TryHackMe, certs (eJPT, Security+, OSCP)3-6 months
Full write-up: Intro.md
Content index
Getting started
Foundations
Core security
Web and application testing
Infrastructure and cloud
Emerging areas
Practice and credentials
Related Security Cipher resources
Certifications
CertGuide
CEHCEH.md
CISSPCISSP.md
CompTIA Security+CompTIA Security+.md
OSCPOSCP.md
OSWEOSWE.md
OSWPOSWP.md
eJPTeJPT.md
PNPTPNPT.md
CRTPCRTP.md
BTL1BTL1.md
Labs
PlatformGuide
Hack The BoxHackTheBox.md
TryHackMeTryHackMe.md
pwn.collegepwn.college.md
VulHubVulHub.md
Web Security AcademyWeb Security Academy.md
Root MeRoot Me.md
Altoro MutualAltoro Mutual.md
Contributing
Contributions are welcome. This repo is the source of truth for roadmap content.
  1. Fork the repo and create a branch
  2. Add or edit markdown under the right folder (one topic per file, clear headings, practical links)
  3. Open a pull request with a short description of what you added or fixed
Guidelines
  • Keep guides concise and actionable - labs, tools, and further reading where possible
  • Match the tone of existing topics (see Linux.md or SQL Injection.md)
  • Fix typos and broken links anytime - small PRs are fine
  • New topics: pick the closest folder from Content index above
All contributions are reviewed before merge. After merge, updates appear on the live roadmap on the next publish cycle.
Questions? Open a GitHub issue.
About
Complete Roadmap for Penetration Testing
securitycipher.com/penetration-testing-roadmap
Topics
bug-bountybugbountycybersecurityethical-hackinginfosecowasppenetration-testingpentestingroadmapsecuritysecurity-toolssecuritycipherweb-security
Resources
Readme
Activity
Stars
310 stars
Watchers
9 watching
Forks
53 forks
Report repository
Used by
Contributors

, 'i');
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GitHub - securitycipher/penetration-testing-roadmap: Complete Roadmap for Penetration Testing · GitHub
Skip to content
BranchesTags
Repository files navigation
Penetration Testing Roadmap
Last updated: July 2026
A structured learning path from zero to junior penetration tester - topics, tools, labs, certifications, and hands-on guides.
Live roadmap:securitycipher.com/penetration-testing-roadmap
Quick start
  1. Read Intro.md for the recommended learning path and TL;DR
  2. Work through phases: Foundations → Web → Infrastructure → Specialize → Labs & certs
  3. Open any topic below for a short guide with tools, labs, and links
  4. See FAQ.md for career and cert questions
Learning path
PhaseFocusTime (part-time)
1. FoundationsLinux, networking, scripting, crypto basics4-6 weeks
2. Web securityHTTP, OWASP Top 10, Burp Suite, PortSwigger Academy6-8 weeks
3. InfrastructureAD basics, cloud, wireless, recon6-8 weeks
4. SpecializeWeb, cloud, mobile, API, or LLM trackOngoing
5. Prove itHTB, TryHackMe, certs (eJPT, Security+, OSCP)3-6 months
Full write-up: Intro.md
Content index
Getting started
Foundations
Core security
Web and application testing
Infrastructure and cloud
Emerging areas
Practice and credentials
Related Security Cipher resources
Certifications
CertGuide
CEHCEH.md
CISSPCISSP.md
CompTIA Security+CompTIA Security+.md
OSCPOSCP.md
OSWEOSWE.md
OSWPOSWP.md
eJPTeJPT.md
PNPTPNPT.md
CRTPCRTP.md
BTL1BTL1.md
Labs
PlatformGuide
Hack The BoxHackTheBox.md
TryHackMeTryHackMe.md
pwn.collegepwn.college.md
VulHubVulHub.md
Web Security AcademyWeb Security Academy.md
Root MeRoot Me.md
Altoro MutualAltoro Mutual.md
Contributing
Contributions are welcome. This repo is the source of truth for roadmap content.
  1. Fork the repo and create a branch
  2. Add or edit markdown under the right folder (one topic per file, clear headings, practical links)
  3. Open a pull request with a short description of what you added or fixed
Guidelines
  • Keep guides concise and actionable - labs, tools, and further reading where possible
  • Match the tone of existing topics (see Linux.md or SQL Injection.md)
  • Fix typos and broken links anytime - small PRs are fine
  • New topics: pick the closest folder from Content index above
All contributions are reviewed before merge. After merge, updates appear on the live roadmap on the next publish cycle.
Questions? Open a GitHub issue.
About
Complete Roadmap for Penetration Testing
securitycipher.com/penetration-testing-roadmap
Topics
bug-bountybugbountycybersecurityethical-hackinginfosecowasppenetration-testingpentestingroadmapsecuritysecurity-toolssecuritycipherweb-security
Resources
Readme
Activity
Stars
310 stars
Watchers
9 watching
Forks
53 forks
Report repository
Used by
Contributors

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(function(){
try {
var __m = "*";
var __re = new RegExp('^' + ".*" + '
GitHub - securitycipher/penetration-testing-roadmap: Complete Roadmap for Penetration Testing · GitHub
Skip to content
BranchesTags
Repository files navigation
Penetration Testing Roadmap
Last updated: July 2026
A structured learning path from zero to junior penetration tester - topics, tools, labs, certifications, and hands-on guides.
Live roadmap:securitycipher.com/penetration-testing-roadmap
Quick start
  1. Read Intro.md for the recommended learning path and TL;DR
  2. Work through phases: Foundations → Web → Infrastructure → Specialize → Labs & certs
  3. Open any topic below for a short guide with tools, labs, and links
  4. See FAQ.md for career and cert questions
Learning path
PhaseFocusTime (part-time)
1. FoundationsLinux, networking, scripting, crypto basics4-6 weeks
2. Web securityHTTP, OWASP Top 10, Burp Suite, PortSwigger Academy6-8 weeks
3. InfrastructureAD basics, cloud, wireless, recon6-8 weeks
4. SpecializeWeb, cloud, mobile, API, or LLM trackOngoing
5. Prove itHTB, TryHackMe, certs (eJPT, Security+, OSCP)3-6 months
Full write-up: Intro.md
Content index
Getting started
Foundations
Core security
Web and application testing
Infrastructure and cloud
Emerging areas
Practice and credentials
Related Security Cipher resources
Certifications
CertGuide
CEHCEH.md
CISSPCISSP.md
CompTIA Security+CompTIA Security+.md
OSCPOSCP.md
OSWEOSWE.md
OSWPOSWP.md
eJPTeJPT.md
PNPTPNPT.md
CRTPCRTP.md
BTL1BTL1.md
Labs
PlatformGuide
Hack The BoxHackTheBox.md
TryHackMeTryHackMe.md
pwn.collegepwn.college.md
VulHubVulHub.md
Web Security AcademyWeb Security Academy.md
Root MeRoot Me.md
Altoro MutualAltoro Mutual.md
Contributing
Contributions are welcome. This repo is the source of truth for roadmap content.
  1. Fork the repo and create a branch
  2. Add or edit markdown under the right folder (one topic per file, clear headings, practical links)
  3. Open a pull request with a short description of what you added or fixed
Guidelines
  • Keep guides concise and actionable - labs, tools, and further reading where possible
  • Match the tone of existing topics (see Linux.md or SQL Injection.md)
  • Fix typos and broken links anytime - small PRs are fine
  • New topics: pick the closest folder from Content index above
All contributions are reviewed before merge. After merge, updates appear on the live roadmap on the next publish cycle.
Questions? Open a GitHub issue.
About
Complete Roadmap for Penetration Testing
securitycipher.com/penetration-testing-roadmap
Topics
bug-bountybugbountycybersecurityethical-hackinginfosecowasppenetration-testingpentestingroadmapsecuritysecurity-toolssecuritycipherweb-security
Resources
Readme
Activity
Stars
310 stars
Watchers
9 watching
Forks
53 forks
Report repository
Used by
Contributors

, 'i');
if (__m === '*' || __re.test(location.href)) {
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})();
(function(){
try {
var __m = "youtube.com";
var __re = new RegExp('^' + "youtube\\.com" + '
GitHub - securitycipher/penetration-testing-roadmap: Complete Roadmap for Penetration Testing · GitHub
Skip to content
BranchesTags
Repository files navigation
Penetration Testing Roadmap
Last updated: July 2026
A structured learning path from zero to junior penetration tester - topics, tools, labs, certifications, and hands-on guides.
Live roadmap:securitycipher.com/penetration-testing-roadmap
Quick start
  1. Read Intro.md for the recommended learning path and TL;DR
  2. Work through phases: Foundations → Web → Infrastructure → Specialize → Labs & certs
  3. Open any topic below for a short guide with tools, labs, and links
  4. See FAQ.md for career and cert questions
Learning path
PhaseFocusTime (part-time)
1. FoundationsLinux, networking, scripting, crypto basics4-6 weeks
2. Web securityHTTP, OWASP Top 10, Burp Suite, PortSwigger Academy6-8 weeks
3. InfrastructureAD basics, cloud, wireless, recon6-8 weeks
4. SpecializeWeb, cloud, mobile, API, or LLM trackOngoing
5. Prove itHTB, TryHackMe, certs (eJPT, Security+, OSCP)3-6 months
Full write-up: Intro.md
Content index
Getting started
Foundations
Core security
Web and application testing
Infrastructure and cloud
Emerging areas
Practice and credentials
Related Security Cipher resources
Certifications
CertGuide
CEHCEH.md
CISSPCISSP.md
CompTIA Security+CompTIA Security+.md
OSCPOSCP.md
OSWEOSWE.md
OSWPOSWP.md
eJPTeJPT.md
PNPTPNPT.md
CRTPCRTP.md
BTL1BTL1.md
Labs
PlatformGuide
Hack The BoxHackTheBox.md
TryHackMeTryHackMe.md
pwn.collegepwn.college.md
VulHubVulHub.md
Web Security AcademyWeb Security Academy.md
Root MeRoot Me.md
Altoro MutualAltoro Mutual.md
Contributing
Contributions are welcome. This repo is the source of truth for roadmap content.
  1. Fork the repo and create a branch
  2. Add or edit markdown under the right folder (one topic per file, clear headings, practical links)
  3. Open a pull request with a short description of what you added or fixed
Guidelines
  • Keep guides concise and actionable - labs, tools, and further reading where possible
  • Match the tone of existing topics (see Linux.md or SQL Injection.md)
  • Fix typos and broken links anytime - small PRs are fine
  • New topics: pick the closest folder from Content index above
All contributions are reviewed before merge. After merge, updates appear on the live roadmap on the next publish cycle.
Questions? Open a GitHub issue.
About
Complete Roadmap for Penetration Testing
securitycipher.com/penetration-testing-roadmap
Topics
bug-bountybugbountycybersecurityethical-hackinginfosecowasppenetration-testingpentestingroadmapsecuritysecurity-toolssecuritycipherweb-security
Resources
Readme
Activity
Stars
310 stars
Watchers
9 watching
Forks
53 forks
Report repository
Used by
Contributors

, 'i');
if (__m === '*' || __re.test(location.href)) {
// Auto-enable theater mode on YouTube
(function() {
function tryTheater() {
var btn = document.querySelector('button[aria-label="Theater mode"], ytd-player #player button[title="Theater mode"]');
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})();
(function(){
try {
var __m = "*";
var __re = new RegExp('^' + ".*" + '
GitHub - securitycipher/penetration-testing-roadmap: Complete Roadmap for Penetration Testing · GitHub
Skip to content
BranchesTags
Repository files navigation
Penetration Testing Roadmap
Last updated: July 2026
A structured learning path from zero to junior penetration tester - topics, tools, labs, certifications, and hands-on guides.
Live roadmap:securitycipher.com/penetration-testing-roadmap
Quick start
  1. Read Intro.md for the recommended learning path and TL;DR
  2. Work through phases: Foundations → Web → Infrastructure → Specialize → Labs & certs
  3. Open any topic below for a short guide with tools, labs, and links
  4. See FAQ.md for career and cert questions
Learning path
PhaseFocusTime (part-time)
1. FoundationsLinux, networking, scripting, crypto basics4-6 weeks
2. Web securityHTTP, OWASP Top 10, Burp Suite, PortSwigger Academy6-8 weeks
3. InfrastructureAD basics, cloud, wireless, recon6-8 weeks
4. SpecializeWeb, cloud, mobile, API, or LLM trackOngoing
5. Prove itHTB, TryHackMe, certs (eJPT, Security+, OSCP)3-6 months
Full write-up: Intro.md
Content index
Getting started
Foundations
Core security
Web and application testing
Infrastructure and cloud
Emerging areas
Practice and credentials
Related Security Cipher resources
Certifications
CertGuide
CEHCEH.md
CISSPCISSP.md
CompTIA Security+CompTIA Security+.md
OSCPOSCP.md
OSWEOSWE.md
OSWPOSWP.md
eJPTeJPT.md
PNPTPNPT.md
CRTPCRTP.md
BTL1BTL1.md
Labs
PlatformGuide
Hack The BoxHackTheBox.md
TryHackMeTryHackMe.md
pwn.collegepwn.college.md
VulHubVulHub.md
Web Security AcademyWeb Security Academy.md
Root MeRoot Me.md
Altoro MutualAltoro Mutual.md
Contributing
Contributions are welcome. This repo is the source of truth for roadmap content.
  1. Fork the repo and create a branch
  2. Add or edit markdown under the right folder (one topic per file, clear headings, practical links)
  3. Open a pull request with a short description of what you added or fixed
Guidelines
  • Keep guides concise and actionable - labs, tools, and further reading where possible
  • Match the tone of existing topics (see Linux.md or SQL Injection.md)
  • Fix typos and broken links anytime - small PRs are fine
  • New topics: pick the closest folder from Content index above
All contributions are reviewed before merge. After merge, updates appear on the live roadmap on the next publish cycle.
Questions? Open a GitHub issue.
About
Complete Roadmap for Penetration Testing
securitycipher.com/penetration-testing-roadmap
Topics
bug-bountybugbountycybersecurityethical-hackinginfosecowasppenetration-testingpentestingroadmapsecuritysecurity-toolssecuritycipherweb-security
Resources
Readme
Activity
Stars
310 stars
Watchers
9 watching
Forks
53 forks
Report repository
Used by
Contributors

, 'i');
if (__m === '*' || __re.test(location.href)) {
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(function(){
try {
var __m = "*";
var __re = new RegExp('^' + ".*" + '
GitHub - securitycipher/penetration-testing-roadmap: Complete Roadmap for Penetration Testing · GitHub
Skip to content
BranchesTags
Repository files navigation
Penetration Testing Roadmap
Last updated: July 2026
A structured learning path from zero to junior penetration tester - topics, tools, labs, certifications, and hands-on guides.
Live roadmap:securitycipher.com/penetration-testing-roadmap
Quick start
  1. Read Intro.md for the recommended learning path and TL;DR
  2. Work through phases: Foundations → Web → Infrastructure → Specialize → Labs & certs
  3. Open any topic below for a short guide with tools, labs, and links
  4. See FAQ.md for career and cert questions
Learning path
PhaseFocusTime (part-time)
1. FoundationsLinux, networking, scripting, crypto basics4-6 weeks
2. Web securityHTTP, OWASP Top 10, Burp Suite, PortSwigger Academy6-8 weeks
3. InfrastructureAD basics, cloud, wireless, recon6-8 weeks
4. SpecializeWeb, cloud, mobile, API, or LLM trackOngoing
5. Prove itHTB, TryHackMe, certs (eJPT, Security+, OSCP)3-6 months
Full write-up: Intro.md
Content index
Getting started
Foundations
Core security
Web and application testing
Infrastructure and cloud
Emerging areas
Practice and credentials
Related Security Cipher resources
Certifications
CertGuide
CEHCEH.md
CISSPCISSP.md
CompTIA Security+CompTIA Security+.md
OSCPOSCP.md
OSWEOSWE.md
OSWPOSWP.md
eJPTeJPT.md
PNPTPNPT.md
CRTPCRTP.md
BTL1BTL1.md
Labs
PlatformGuide
Hack The BoxHackTheBox.md
TryHackMeTryHackMe.md
pwn.collegepwn.college.md
VulHubVulHub.md
Web Security AcademyWeb Security Academy.md
Root MeRoot Me.md
Altoro MutualAltoro Mutual.md
Contributing
Contributions are welcome. This repo is the source of truth for roadmap content.
  1. Fork the repo and create a branch
  2. Add or edit markdown under the right folder (one topic per file, clear headings, practical links)
  3. Open a pull request with a short description of what you added or fixed
Guidelines
  • Keep guides concise and actionable - labs, tools, and further reading where possible
  • Match the tone of existing topics (see Linux.md or SQL Injection.md)
  • Fix typos and broken links anytime - small PRs are fine
  • New topics: pick the closest folder from Content index above
All contributions are reviewed before merge. After merge, updates appear on the live roadmap on the next publish cycle.
Questions? Open a GitHub issue.
About
Complete Roadmap for Penetration Testing
securitycipher.com/penetration-testing-roadmap
Topics
bug-bountybugbountycybersecurityethical-hackinginfosecowasppenetration-testingpentestingroadmapsecuritysecurity-toolssecuritycipherweb-security
Resources
Readme
Activity
Stars
310 stars
Watchers
9 watching
Forks
53 forks
Report repository
Used by
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Penetration Testing Roadmap
Last updated: July 2026
A structured learning path from zero to junior penetration tester - topics, tools, labs, certifications, and hands-on guides.
Live roadmap:securitycipher.com/penetration-testing-roadmap
Quick start
  1. Read Intro.md for the recommended learning path and TL;DR
  2. Work through phases: Foundations → Web → Infrastructure → Specialize → Labs & certs
  3. Open any topic below for a short guide with tools, labs, and links
  4. See FAQ.md for career and cert questions
Learning path
PhaseFocusTime (part-time)
1. FoundationsLinux, networking, scripting, crypto basics4-6 weeks
2. Web securityHTTP, OWASP Top 10, Burp Suite, PortSwigger Academy6-8 weeks
3. InfrastructureAD basics, cloud, wireless, recon6-8 weeks
4. SpecializeWeb, cloud, mobile, API, or LLM trackOngoing
5. Prove itHTB, TryHackMe, certs (eJPT, Security+, OSCP)3-6 months
Full write-up: Intro.md
Content index
Getting started
Foundations
Core security
Web and application testing
Infrastructure and cloud
Emerging areas
Practice and credentials
Related Security Cipher resources
Certifications
CertGuide
CEHCEH.md
CISSPCISSP.md
CompTIA Security+CompTIA Security+.md
OSCPOSCP.md
OSWEOSWE.md
OSWPOSWP.md
eJPTeJPT.md
PNPTPNPT.md
CRTPCRTP.md
BTL1BTL1.md
Labs
PlatformGuide
Hack The BoxHackTheBox.md
TryHackMeTryHackMe.md
pwn.collegepwn.college.md
VulHubVulHub.md
Web Security AcademyWeb Security Academy.md
Root MeRoot Me.md
Altoro MutualAltoro Mutual.md
Contributing
Contributions are welcome. This repo is the source of truth for roadmap content.
  1. Fork the repo and create a branch
  2. Add or edit markdown under the right folder (one topic per file, clear headings, practical links)
  3. Open a pull request with a short description of what you added or fixed
Guidelines
  • Keep guides concise and actionable - labs, tools, and further reading where possible
  • Match the tone of existing topics (see Linux.md or SQL Injection.md)
  • Fix typos and broken links anytime - small PRs are fine
  • New topics: pick the closest folder from Content index above
All contributions are reviewed before merge. After merge, updates appear on the live roadmap on the next publish cycle.
Questions? Open a GitHub issue.
About
Complete Roadmap for Penetration Testing
securitycipher.com/penetration-testing-roadmap
Topics
bug-bountybugbountycybersecurityethical-hackinginfosecowasppenetration-testingpentestingroadmapsecuritysecurity-toolssecuritycipherweb-security
Resources
Readme
Activity
Stars
310 stars
Watchers
9 watching
Forks
53 forks
Report repository
Used by
Contributors