Penetration Testing Roadmap (Daily - 5 Hours)

Week 1-2: Core Foundations (Networking, Linux, Basics)

Day 1: Intro to cybersecurity + hacking types

- TryHackMe: https://tryhackme.com/room/presecurity

Day 2: Networking basics - IP, TCP, ports, DNS

- TryHackMe: https://tryhackme.com/room/presecurity

Day 3: OSI Model, HTTP, web basics

- Wireshark: https://www.wireshark.org/

Day 4: Linux CLI basics

- TryHackMe: https://tryhackme.com/room/linuxfundamentals1

Day 5: Linux files, permissions

- TryHackMe: https://tryhackme.com/room/linuxfundamentals2

Day 6: Bash scripting basics

- YouTube: Search "Bash scripting for beginners"

Day 7: Practice on OverTheWire

- Bandit: https://overthewire.org/wargames/bandit/

Week 3-4: Networking Tools + Recon

Day 8: Nmap basics

- TryHackMe: https://tryhackme.com/room/nmap

Day 9: Nmap scripts + scanning

- https://nmap.org/nsedoc/
 Penetration Testing Roadmap (Daily - 5 Hours)

Day 10: Whois, theHarvester, DNS enum

- TryHackMe: https://tryhackme.com/room/passiverecon

Day 11: Subdomain enum

- Sublist3r: https://github.com/aboul3la/Sublist3r

Day 12: Directory brute-force (Dirb, Gobuster)

- Gobuster: https://github.com/OJ/gobuster

Day 13: Recon challenge

- Create your own VM or use TryHackMe

Day 14: Full recon-focused CTF

- TryHackMe: https://tryhackme.com/room/ice

- HTB: https://app.hackthebox.com/starting-point

Week 5-6: Vulnerability Scanning + Exploitation Tools

Day 15: Service enumeration (FTP/SSH/SMB)

- TryHackMe: https://tryhackme.com/room/basicpentestingjt

Day 16: FTP exploits

- Metasploit: https://docs.rapid7.com/metasploit/

Day 17: SSH bruteforce with Hydra

- Hydra: https://github.com/vanhauser-thc/thc-hydra

Day 18: SMB enumeration

- Enum4linux: https://tools.kali.org/information-gathering/enum4linux
 Penetration Testing Roadmap (Daily - 5 Hours)

Day 19: Searchsploit, ExploitDB

- https://www.exploit-db.com/

Day 20: Metasploit usage

- TryHackMe: https://tryhackme.com/room/metasploitintro

Day 21: Full exploitation practice

- TryHackMe: https://tryhackme.com/room/vulnversity

Week 7-8: Web Application Pentesting

Day 22: HTTP requests and architecture

- TryHackMe: https://tryhackme.com/room/webfundamentals

Day 23: Burp Suite basics

- https://portswigger.net/burp

Day 24: OWASP Top 10 overview

- https://owasp.org/www-project-top-ten/

Day 25: Cross-site scripting (XSS)

- https://portswigger.net/web-security/cross-site-scripting

Day 26: SQL injection

- https://portswigger.net/web-security/sql-injection

Day 27: File Upload, Command Injection

- DVWA: http://www.dvwa.co.uk/

Day 28: IDOR + Authentication Bypass

- https://portswigger.net/web-security/access-control/idor
 Penetration Testing Roadmap (Daily - 5 Hours)

Week 9-10: Privilege Escalation

Day 29: Linux privesc intro

- TryHackMe: https://tryhackme.com/room/linuxprivesc

Day 30: SUID, PATH, cron jobs

- GTFOBins: https://gtfobins.github.io/

Day 31: LinPEAS scanning

- https://github.com/carlospolop/PEASS-ng

Day 32: Windows privesc intro

- TryHackMe: https://tryhackme.com/room/windows10privesc

Day 33: WinPEAS

- https://github.com/carlospolop/PEASS-ng/tree/master/winPEAS

Day 34: Registry, Scheduled Tasks

- TryHackMe: custom VMs or VulnHub

Day 35: Practice box with privesc

- VulnHub: https://www.vulnhub.com/

Week 11-12: Full Attack Chains + Reporting

Day 36: Post Exploitation

- https://tryhackme.com/room/postexploit

Day 37: Pivoting + lateral movement

- HackTheBox Academy or custom labs

Day 38: TryHackMe Offensive Pentesting

- https://tryhackme.com/path/outline/offensivepentesting

Day 39: Reporting fundamentals

- Sample template: https://github.com/honze-net/nmap-bootstrap-xsl

Day 40: Write practice pentest report

- Use Markdown or Google Docs

Day 41: TryHackMe RootMe

- https://tryhackme.com/room/rrootme

Day 42: HackTheBox Starting Point

- https://app.hackthebox.com/starting-point

Final Notes

Certifications:

- eJPT: https://ine.com/pages/ejpt

- PNPT: https://www.tcm-sec.com/pnpt/

- OSCP: https://www.offsec.com/oscp/

Document notes:

- Obsidian: https://obsidian.md/

- CherryTree: https://www.giuspen.com/cherrytree/

Portfolio tips:

- GitHub + blog with screenshots and reports