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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.

While engaging in pentesting can be an exhilarating experience, it is crucial to grasp the art of delivering maximum value during such assessments. While clients do expect you to exploit vulnerabilities in their systems, they also seek a comprehensive understanding of the risks associated with those vulnerabilities. Simply boasting about successfully sniffing credentials through LLMNR poisoning and cracking a domain admin’s account or leveraging XSS and CSRF for RCE, though impressive, falls short of meeting their expectations. What truly matters is explaining the significance of the identified vulnerabilities and their potential impact on the client’s business.

Rather than merely stating “I gained domain administrator privileges,” it is more impactful to elucidate how this could enable an attacker to access sensitive HR records or client social security numbers when infiltrating a web application or file server. By providing such context, the severity and implications of the security flaw become crystal clear.

Furthermore, it’s vital to recognize that each pentest may have specific goals tailored to the client’s needs. Understanding the client’s motivations for conducting the pentest is essential. They might already have an internal pentesting process and require a third-party assessment to fulfill a compliance requirement. Alternatively, they could be assessing the efficiency of their IT security team. Being aware of these background details allows you to customize your methodology accordingly.

In essence, successful pentesting involves not only showcasing technical expertise but also presenting findings in a manner that highlights their real-world impact on the client’s business. Tailoring the assessment to align with the client’s goals ensures a meaningful and valuable engagement.