Penetration Testing Guide

Master penetration testing methodologies, security assessment techniques, and ethical hacking best practices

Penetration Testing Basics

Penetration testing (pen testing) is a simulated cyber attack against your computer system to check for exploitable vulnerabilities.

Types of Penetration Testing

Black Box Testing

Tester has no prior knowledge of the target system. Simulates external attacker perspective.

White Box Testing

Tester has full knowledge of the system architecture, source code, and documentation.

Gray Box Testing

Tester has partial knowledge of the system, simulating an insider threat scenario.

External Testing

Tests external-facing assets like web applications, email servers, and VPNs.

Internal Testing

Tests internal network security from within the organization's perimeter.

Social Engineering

Tests human vulnerabilities through phishing, pretexting, and other techniques.

Penetration Testing vs Vulnerability Assessment

AspectPenetration TestingVulnerability Assessment
ScopeFocused on specific targetsBroad system-wide scan
MethodManual exploitation attemptsAutomated scanning tools
DepthDeep dive into vulnerabilitiesSurface-level identification
TimeDays to weeksHours to days

Penetration Testing Methodology

Following a structured methodology ensures comprehensive coverage and consistent results in penetration testing engagements.

OWASP Testing Guide

Phase 1: Information Gathering

Collect information about the target through passive and active reconnaissance.

Phase 2: Configuration and Deployment Management Testing

Test for misconfigurations in web servers, application servers, and databases.

Phase 3: Identity Management Testing

Test user registration, password recovery, and account management processes.

Phase 4: Authentication Testing

Test authentication mechanisms for weaknesses and bypasses.

Phase 5: Authorization Testing

Test access controls and privilege escalation vulnerabilities.

NIST SP 800-115 Framework

Planning

  • • Define scope and objectives
  • • Obtain proper authorization
  • • Gather requirements
  • • Create testing plan

Discovery

  • • Network discovery
  • • Port scanning
  • • Service enumeration
  • • Vulnerability identification

Attack

  • • Exploit vulnerabilities
  • • Gain access
  • • Escalate privileges
  • • Maintain access

Reconnaissance

Reconnaissance is the first phase of penetration testing, involving information gathering about the target system or organization.

Passive Reconnaissance

OSINT (Open Source Intelligence)

  • • Company websites and social media
  • • Job postings and employee information
  • • Public databases and registries
  • • News articles and press releases

DNS Enumeration

  • • DNS record analysis
  • • Subdomain discovery
  • • Zone transfers
  • • Reverse DNS lookups

Search Engine Reconnaissance

  • • Google dorking
  • • Shodan searches
  • • Certificate transparency logs
  • • Archive.org snapshots

Active Reconnaissance

Network Scanning

  • • Port scanning (Nmap)
  • • Service enumeration
  • • OS fingerprinting
  • • Vulnerability scanning

Web Application Reconnaissance

  • • Directory enumeration
  • • Technology stack identification
  • • Error message analysis
  • • Input validation testing

Social Engineering

  • • Phishing campaigns
  • • Pretexting
  • • Physical security testing
  • • Dumpster diving

Wireless Reconnaissance

  • • WiFi network discovery
  • • Access point analysis
  • • Signal strength mapping
  • • Client device enumeration

Vulnerability Assessment

Vulnerability assessment involves identifying, classifying, and prioritizing security vulnerabilities in systems and applications.

Common Vulnerability Categories

OWASP Top 10

Most critical web application security risks including injection, broken authentication, and sensitive data exposure.

CVE (Common Vulnerabilities and Exposures)

Publicly known information security vulnerabilities and exposures.

Configuration Issues

Misconfigurations in servers, applications, and network devices.

Business Logic Flaws

Vulnerabilities in application logic and business processes.

Vulnerability Scoring

CVSS (Common Vulnerability Scoring System)

  • • Base Score: Intrinsic characteristics
  • • Temporal Score: Time-dependent factors
  • • Environmental Score: Organization-specific
  • • Scale: 0.0 (low) to 10.0 (critical)

Risk Assessment

  • • Likelihood of exploitation
  • • Impact on business operations
  • • Asset criticality
  • • Remediation cost and effort

Exploitation

Exploitation involves attempting to compromise identified vulnerabilities to demonstrate their impact and validate security controls.

Exploitation Techniques

Web Application Exploitation

  • • SQL injection attacks
  • • Cross-site scripting (XSS)
  • • Cross-site request forgery (CSRF)
  • • File upload vulnerabilities
  • • Authentication bypass

Network Exploitation

  • • Buffer overflow attacks
  • • Man-in-the-middle attacks
  • • ARP spoofing
  • • DNS poisoning
  • • Wireless attacks

System Exploitation

  • • Privilege escalation
  • • Lateral movement
  • • Persistence mechanisms
  • • Data exfiltration
  • • Rootkit installation

Social Engineering

  • • Phishing campaigns
  • • Pretexting attacks
  • • Baiting techniques
  • • Tailgating
  • • Impersonation

Post-Exploitation

Maintaining Access

  • • Backdoor installation
  • • User account creation
  • • Service persistence
  • • Scheduled task creation

Covering Tracks

  • • Log file modification
  • • Event log clearing
  • • File timestamp manipulation
  • • Network traffic obfuscation

Reporting & Remediation

Effective reporting and remediation planning are crucial for translating penetration test results into actionable security improvements.

Report Structure

Executive Summary

High-level overview of findings, risk assessment, and recommendations for management.

Technical Details

Detailed technical findings, proof-of-concept exploits, and remediation steps.

Risk Assessment

Risk ratings, business impact analysis, and likelihood of exploitation.

Remediation Plan

Prioritized action items, timelines, and resource requirements for fixing vulnerabilities.

Remediation Best Practices

Immediate Actions

  • Patch critical vulnerabilities immediately
  • Implement temporary mitigations
  • Monitor for exploitation attempts
  • Notify relevant stakeholders

Long-term Improvements

  • Implement security controls
  • Enhance monitoring and detection
  • Conduct security training
  • Establish regular testing schedule

Penetration Testing Tools

Use our comprehensive security tools to perform penetration testing and vulnerability assessments:

Website Security Scanner

Comprehensive website security vulnerability scanner with detailed reporting and recommendations.

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Port Scanner

Scan open ports on any IP address or hostname to identify potential security risks.

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Subdomain Finder

Discover subdomains of any domain to map the complete attack surface.

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Security Headers Checker

Analyze HTTP security headers and get detailed security recommendations.

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