Penetration testing, or pentesting, is a systematic process that involves several distinct phases. Each phase is crucial for ensuring a thorough assessment of the security posture of the target system or application. Below, we will explore each phase in detail:

• Objective Setting: Define the scope and goals of the pentest.
• Rules of Engagement: Establish guidelines, including what is in scope, the testing schedule, and communication protocols.
• Authorization: Obtain written permission from the target organization to conduct the pentest.

Before starting a pentest, a tester might receive a document outlining the specific IP addresses and applications that are within scope, as well as the testing window (e.g., "Testing will occur between 10 PM and 6 AM to minimize disruption").

• Task: Draft a sample Rules of Engagement document for a pentest on a web application.
• Solution: Ensure the document includes scope, testing schedule, communication protocols, and authorization.

• Passive Reconnaissance: Collect information without directly interacting with the target (e.g., using WHOIS, DNS records).
• Active Reconnaissance: Interact with the target to gather information (e.g., ping sweeps, port scans).

Using a tool like whois to gather domain registration information or nslookup to find DNS records.

• Task: Use whois to gather information about a domain of your choice.
• Solution: Document the registrar, registration date, and contact information.

• Port Scanning: Identify open ports on the target system (e.g., using nmap).
• Service Enumeration: Determine what services are running on the open ports (e.g., using nmap -sV).
• Vulnerability Scanning: Identify potential vulnerabilities in the services (e.g., using Nessus).

Running nmap -sS -p 1-65535 target_ip to perform a TCP SYN scan on all ports.

• Task: Perform a port scan on a local machine using nmap.
• Solution: Document the open ports and the services running on them.

• Exploitation: Attempt to exploit identified vulnerabilities to gain unauthorized access.
• Payloads: Code that is executed on the target system after exploitation (e.g., reverse shells).

Using Metasploit to exploit a known vulnerability in a web application.

• Task: Use Metasploit to exploit a vulnerable service in a controlled lab environment.
• Solution: Document the steps taken and the outcome of the exploitation.

• Privilege Escalation: Gain higher-level access on the target system.
• Maintaining Access: Establish a persistent presence on the target system.
• Covering Tracks: Remove evidence of the pentest activities.

Using a local privilege escalation exploit to gain root access on a Linux system.

• Task: Perform a privilege escalation on a vulnerable system in a controlled lab environment.
• Solution: Document the steps taken and the outcome.

• Documentation: Record all findings, including vulnerabilities and exploitation steps.
• Remediation Recommendations: Provide actionable steps to fix identified vulnerabilities.
• Presentation: Communicate the results to stakeholders in a clear and concise manner.

Creating a report that includes an executive summary, detailed findings, and remediation steps.

• Task: Draft a sample report for a pentest on a web application.
• Solution: Ensure the report includes an executive summary, detailed findings, and remediation recommendations.

Understanding the phases of pentesting is crucial for conducting a thorough and effective security assessment. Each phase builds upon the previous one, ensuring a comprehensive evaluation of the target system or application. In the next module, we will delve deeper into the techniques and tools used during the reconnaissance and information gathering phase.