Web Application Penetration Testing Process

2. Pre-engagement

2.1 Define Scope

• Objectives: Identify what assets (web applications, APIs) will be tested.
• Constraints: Legal and operational constraints to be considered.
• Rules of Engagement: Define acceptable testing methods and timelines.

2.2 Gather Information

• Documentation Review: Analyze architecture, data flow diagrams, and security policies.

• Identify Stakeholders: Understand the roles and responsibilities within the testing environment.

3. Reconnaissance

Gathering information about a target.

3.1 Passive Reconnaissance

Passive reconnaissance in web penetration testing involves gathering information about a target without directly interacting with it, thereby minimizing the risk of detection.

• DNS Footprinting: Tools: dig, nslookup, Sublist3r
• WHOIS Lookup: Tools: whois
• Social Engineering: Gather information from social media and public profiles.
• Google Dorking: Utilizing advanced search operators to find specific information about the target.
• Public Repositories [GitHub, GitLab, Bitbucket]: Searching for exposed code, credentials, and other sensitive information.
• Metadata Extractors: Tools: ExifTool: Extracting metadata from documents, images, and other files. FOCA: Extracting metadata and hidden information from public documents.
• Web Archive Services: Tools: Wayback Machine: Viewing historical versions of web pages. Archive.today Netcraft: Capturing and viewing past versions of websites.
• Public Data Breaches: Tools: Have I Been Pwned: Checking if emails or domains have been involved in data breaches. DeHashed: Searching for leaked credentials and other sensitive data.
• Reconnaissance Frameworks: Tools: Recon-ng: A full-featured reconnaissance framework written in Python. theHarvester: An open-source intelligence gathering tool.
• OWASP Web Application Testing Guide

3.2 Active Reconnaissance

Active reconnaissance (active recon) refers to a method used in the context of cybersecurity to gather information about a target system or network by directly interacting with it.

• Port Scanning: Tools: Nmap, Masscan: A powerful network scanning tools used to discover hosts, open ports, and services running on those ports.
• Service Enumeration: Tools: Nmap, Netcat: Identifying specific services running on open ports to gather detailed information about versions and configurations.
• Vulnerability Scanning: Tools: Nessus OpenVAS Nikto Burpsuite OWASP ZAP : Using automated tools to scan for known vulnerabilities in web applications and services.
• Directory and File Brute Forcing: Tools: DirBuster Gobuster: Actively searching for hidden directories and files on a web server.
• Web Crawling and Spidering: Tools: OWASP ZAP Spider: Automatically navigating through web application links to map the structure and discover hidden pages.
• OWASP Web Application Testing Guide

4. Threat Modeling

Threat modeling is a structured process used to identify, evaluate, and mitigate potential security threats and vulnerabilities in a system, application or network. The goal of threat modeling is to understand and address security risks early in the development lifecycle, thereby improving the overall security posture of the system. This proactive approach helps organizations anticipate potential attacks and design effective defenses.

4.1 Identify Threats

• Attack Surface Analysis: Map out the application’s attack vectors.
• Data Classification: Determine the sensitivity of data processed by the application.

Process:

• OWASP Threat Modelling Process
• Microsoft Threat Modelling Process

4.2 Vulnerability Assessment

A vulnerability assessment is a systematic process used to identify, evaluate and prioritize vulnerabilities in a system, network or application. The goal is to discover weaknesses that could be exploited by attackers and provide recommendations for mitigating these risks.

• Common Vulnerabilities: OWASP Top 10, SANS Top 25
• Automated Scanning: Tools: Nessus OpenVAS Burpsuite Nikto

OWASP:

• Web Top 10
• API Top 10

SANS:

• SANS Top 25

5. Penetration Testing

The primary goal is to identify and exploit vulnerabilities in order to understand their potential impact and provide recommendations for improving security.

OWASP Web Application Testing Guide

6. Post-Exploitation

Post-exploitation refers to the stage in the hacking process that occurs after an attacker has successfully compromised a target system. During this phase, the attacker focuses on consolidating their control, gathering valuable information, and preparing for future operations. The primary objectives of post-exploitation include maintaining access, escalating privileges, exfiltrating data, and covering tracks to avoid detection.

6.1 Persistence

• Backdoors: Check if the attacker can maintain access.
• Rootkits: Analyze for the presence of rootkits.
• Maintaining Access:
  • Persistence Mechanisms: Installing backdoors, rootkits, or other persistent access tools to ensure continued access even after reboots or other interruptions.
  • Creating User Accounts: Creating hidden or low-privilege user accounts that can be used to regain access without raising suspicion.
• Privilege Escalation:
  • Exploiting Vulnerabilities: Identifying and exploiting additional vulnerabilities to gain higher levels of access and control within the compromised system.
  • Credential Dumping: Extracting passwords, hashes, or other authentication tokens to access more privileged accounts.
• Internal Reconnaissance:
  • Network Mapping: Mapping the internal network to identify other valuable targets, such as servers, databases, and sensitive information.
  • Enumeration: Gathering detailed information about the system, such as installed software, running services, and connected devices.
• Data Exfiltration:
  • Sensitive Data Exposure: Tools: Wireshark Tcpdump
  • Data Integrity: Ensure data has not been tampered with during transmission.
• Lateral Movement:
  • Pivoting: Using the compromised system as a foothold to move laterally across the network, compromising additional systems.
  • Exploiting Trust Relationships: Taking advantage of trusted relationships between systems to move undetected.
• Covering Tracks:
  • Log Manipulation: Altering or deleting log files to remove evidence of the attacker’s activities.
  • Clearing Traces: Removing malware, scripts or other tools used during the attack to prevent detection and analysis.
  • Obfuscation: Using techniques like encryption, steganography and file obfuscation to hide malicious activities.

7. Reporting

7.1 Findings Documentation

• Vulnerability Details: Description, severity, impact, and evidence[PoC].
• Remediation Steps: Detailed steps to mitigate identified vulnerabilities.

7.2 Executive Summary

• Overview: High-level summary of findings and recommendations.
• Risk Assessment: Impact analysis and risk rating.

8. Remediation

8.1 Fix Identified Issues

• Patching: Apply necessary patches and updates.
• Configuration Changes: Adjust settings to enhance security.

8.2 Verification

• Re-testing: Verify that all issues have been addressed.
• Regression Testing: Ensure no new issues have been introduced.

9. Continuous Improvement

9.1 Lessons Learned

• Incident Review: Analyze past incidents to improve future response.
• Process Refinement: Continuously refine testing and security processes.

9.2 Staying Updated

• Security Feeds: Follow security news and updates from sources like OWASP, SANS.
• Community Engagement: Participate in security forums and conferences | BlackHat , Nullcon.

This comprehensive guide ensures a thorough approach to web application penetration testing, covering all necessary aspects from reconnaissance to continuous improvement.

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