Having a structured process or checklist and adhering to it is paramount when conducting a penetration test. This methodology remains consistent across different engagements or target machines. The process typically involves identifying IPs/hostnames, performing port scans to uncover exposed services, and utilizing various tools to further investigate these services.

For instance, when encountering a web server, conducting directory brute-force with wfuzz can reveal available paths, followed by running additional scripts to determine the underlying technologies. Similarly, if a Windows box with SMB exposure is found, Enum4Linux can be employed to check for null sessions and obtain a list of Active Directory objects. Additionally, scripts may be used to assess vulnerabilities with publicly available exploits.

Understanding the inner workings of each service and the appropriate tools to extract more information and exploit them is critical. The process should be dynamic, evolving as you learn about new enumeration and exploitation techniques. Future sections in this blog will offer commands and processes tailored to specific technologies frequently encountered during such engagements.

Here are some additional tips for an effective workflow:

  1. Keep scans running continually, ensuring that you have a quick nmap scan on the box while exploring a web server or utilizing Aquatone to screenshot the root directory pages of all web servers within a larger scope.
  2. Organize scans by creating a separate folder for each target box and saving all scan results to a file. This practice prevents redundant rescans and saves valuable time.
  3. Initially, use tools manually to grasp their functionalities fully before automating processes. Understanding protocols, like HTTP headers, before deploying automated scripts is essential for effective and informed testing.
  4. For professional pentesting engagements, consider using a console recording program that documents all commands and their outputs. This provides a “Cover Your Ass” (CYA) measure, especially if the client requests a comprehensive record of the engagement. Having detailed information about the scanning activities can be invaluable in troubleshooting and preventing potential issues.

By following these guidelines and maintaining a well-structured approach, you can impress clients with your meticulousness while delivering comprehensive and impactful penetration test results.