Penetration testing (pentesting) is a structured, authorized simulation of a cyberattack aimed at identifying vulnerabilities in an organization's security posture.

For beginners, the most recognized framework is the Penetration Testing Execution Standard (PTES), which breaks the process into seven distinct phases.

Phase 1: Pre-Engagement Interactions

This phase sets the foundation and legal boundaries for the test. You cannot legally pentest without this.

• Goals: Define the objectives of the test (e.g., compliance validation, finding critical bugs).
• Scope: Define what is being tested (IP addresses, domains, physical locations) and what is off-limits.
• Rules of Engagement (RoE): Establish how you will test (e.g., testing hours, contact points for emergencies, approved tools).
• Legal Documents: Sign NDAs and Contracts authorizing you to perform the testing.

Phase 2: Intelligence Gathering (Reconnaissance)

The goal is to gather as much information as possible about the target to find potential entry points.

• Passive Reconnaissance: Gathering information without directly interacting with the target's systems (e.g., using Google Dorking, OSINT tools like Shodan, LinkedIn, WHOIS lookups).
• Active Reconnaissance: Directly interacting with the target to gather data (e.g., DNS interrogation, subdomain enumeration).

Phase 3: Threat Modeling

Using the gathered intelligence, you build a model to identify the most likely attack vectors and high-value assets.

• Identify Assets: What is the most critical data (databases, customer info)?
• Identify Threats: What types of attackers (hacktivists, competitors) would target this data?
• Attack Mapping: Determine the path of least resistance to reach the high-value assets.

Phase 4: Vulnerability Analysis

This phase involves identifying weaknesses in the target systems.

• Automated Scanning: Using tools like Nessus or OpenVAS to scan for known vulnerabilities.
• Manual Analysis: Investigating the results to eliminate false positives and discovering vulnerabilities that tools miss (e.g., business logic flaws).
• Enumeration: Detailed analysis of services (like the PostgreSQL commands previously discussed) to find misconfigurations or weak credentials.

Phase 5: Exploitation

This is the "hacking" phase where you attempt to bypass security controls to gain access to the system.

• Gaining Access: Attempting to exploit the vulnerabilities identified in Phase 4 (e.g., SQL injection, phishing, brute-forcing passwords).
• Payload Delivery: Using tools like Metasploit to deliver payloads that give you a foothold on the system.

Phase 6: Post-Exploitation

Once access is gained, this phase determines the value of the compromised system and the potential impact of a real attack.

• Privilege Escalation: Attempting to gain higher-level permissions (e.g., moving from a standard user to Administrator or Root).
• Lateral Movement: Moving from the compromised system to other systems within the network.
• Data Exfiltration: Identifying and attempting to steal sensitive data to demonstrate impact.

Phase 7: Reporting

This is the most critical phase for the client. It converts technical findings into business risk.

• Executive Summary: A high-level overview for non-technical stakeholders focusing on business risk.
• Technical Report: Detailed findings, including the attack path, severity ratings (e.g., using CVSS scores), proof-of-concept screenshots, and logs.
• Remediation: Actionable advice on how to fix the identified vulnerabilities.