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Penetration Testing Methodology

Expert25 min readMay 25, 2025
PentestingOWASPSecurity Assessment

Comprehensive guide for professional penetration tests according to OWASP and NIST standards. From planning to reporting – all phases of a successful pentest.

1. Penetration Testing Methodology

Legal Notice

Penetration tests may only be performed with explicit written permission. Unauthorized testing is illegal and may have criminal consequences.

PTES (Penetration Testing Execution Standard)

Pre-Engagement

Scope Definition, Legal Agreements, Rules of Engagement

Intelligence Gathering

OSINT, Reconnaissance, Information Collection

Threat Modeling

Attack Vectors, Asset Valuation, Threat Analysis

Vulnerability Analysis

Scanning, Enumeration, Weakness Identification

Exploitation

Proof of Concept, Access Gaining, Privilege Escalation

Reporting

Documentation, Risk Assessment, Remediation

2. Planning & Reconnaissance Phase

OSINT (Open Source Intelligence)

Information Gathering Checklist

Domain Intelligence
  • • Subdomain Enumeration
  • • DNS Records Analysis
  • • WHOIS Information
  • • Certificate Transparency Logs
  • • Email Addresses
Technical Intelligence
  • • Technology Stack Identification
  • • Public Code Repositories
  • • Social Media Profiles
  • • Job Postings Analysis
  • • Leaked Credentials

Reconnaissance Tools & Commands

# Subdomain Enumeration
subfinder -d target.com -o subdomains.txt
amass enum -d target.com
assetfinder target.com

# DNS Reconnaissance
dig target.com ANY
dnsrecon -d target.com -t std
fierce -dns target.com

# Port Scanning (Initial)
nmap -sn 192.168.1.0/24
masscan -p1-65535 192.168.1.1 --rate=1000

# Web Technology Detection
whatweb target.com
wafw00f target.com
wappalyzer target.com

3. Scanning & Enumeration

Scanning Strategy

Start with passive scans and progress to active scans. Document all findings systematically.

Nmap Scanning Techniques

Target Discovery

# Host Discovery
nmap -sn 192.168.1.0/24
nmap -PS22,80,443 192.168.1.0/24

# TCP SYN Scan (Stealth)
nmap -sS -T4 -p- target.com

# Service Version Detection
nmap -sV -sC -p 1-65535 target.com

# UDP Scan (Top 1000 ports)
nmap -sU --top-ports 1000 target.com

Service Enumeration

# HTTP/HTTPS Enumeration
gobuster dir -u http://target.com -w /usr/share/wordlists/dirb/common.txt
nikto -h http://target.com
dirb http://target.com

# SMB Enumeration
enum4linux target.com
smbclient -L //target.com
smbmap -H target.com

# FTP Enumeration
nmap --script ftp-anon,ftp-bounce,ftp-libopie -p 21 target.com

4. Exploitation & Post-Exploitation

Exploitation Ethics

Only perform proof-of-concept exploits. Avoid causing damage to the target system. Document all steps for the report.

Common Attack Vectors

Web Application Attacks

  • • SQL Injection (SQLi)
  • • Cross-Site Scripting (XSS)
  • • Cross-Site Request Forgery (CSRF)
  • • Local/Remote File Inclusion
  • • Server-Side Request Forgery (SSRF)
  • • Insecure Direct Object References

System-Level Attacks

  • • Buffer Overflow Exploits
  • • Privilege Escalation
  • • Weak Service Configurations
  • • Default Credentials
  • • Unpatched Vulnerabilities
  • • Misconfigured Services

Post-Exploitation Activities

# System Information Gathering
uname -a
cat /etc/passwd
ps aux
netstat -tulpn

# Privilege Escalation Check
sudo -l
find / -perm -u=s -type f 2>/dev/null
getcap -r / 2>/dev/null

# Network Reconnaissance
arp -a
route -n
cat /etc/hosts

# Data Exfiltration (Proof of Concept only)
find / -name "*.txt" -o -name "*.doc" -o -name "*.pdf" 2>/dev/null
locate password
grep -r "password" /var/log/ 2>/dev/null

5. Reporting & Documentation

Report Structure

Executive Summary

  • • High-level overview of findings
  • • Risk assessment matrix
  • • Business impact analysis
  • • Strategic recommendations

Technical Details

  • • Detailed vulnerability descriptions
  • • Proof-of-concept evidence
  • • CVSS scoring and classification
  • • Step-by-step reproduction guides

Remediation

  • • Prioritized remediation roadmap
  • • Technical implementation guides
  • • Compliance mapping (OWASP, NIST)
  • • Timeline recommendations

Risk Classification

CRITICAL
9.0 - 10.0
HIGH
7.0 - 8.9
MEDIUM
4.0 - 6.9
LOW
0.1 - 3.9

6. Essential Penetration Testing Tools

Reconnaissance Tools

NmapNetwork Discovery & Port Scanning
MasscanHigh-Speed Port Scanner
GobusterDirectory/File Enumeration
SubfinderSubdomain Discovery

Exploitation Tools

MetasploitExploitation Framework
Burp SuiteWeb Application Testing
SQLmapSQL Injection Testing
John the RipperPassword Cracking

G-Data Security Tools

G-Data Endpoint ProtectionBehavioral Analysis & Detection
G-Data Security AwarenessPhishing Simulation Platform
G-Data Network SecurityAdvanced Threat Protection

Reporting Tools

DradisCollaboration & Reporting
FaradayVulnerability Management
MagicTreeData Correlation
SerpicoReport Generation

Thalvos Cloud Penetration Testing Services

As certified G-Data Security partners, we offer professional penetration tests with German security standards.

Web App Pentests
OWASP Top 10 compliance
Network Pentests
Infrastructure Assessment
Mobile App Tests
iOS & Android Security

OWASP Top 10 2021

A01Broken Access Control
A02Cryptographic Failures
A03Injection
A04Insecure Design
A05Security Misconfiguration

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