Reconnaissance and enumeration are both equally significant phases of the penetration testing lifecycle. In hindsight, both reconnaissance and enumeration seem to be very similar as the pair involve information gathering. Whilst reconnaissance leverages passive approaches without direct interaction with the target, enumeration exploits susceptibilities and vulnerabilities in direct client-server communication. Both phases involve gathering information and pinpointing the attack surface within the network of the target. To do so, powerful tools such as Nmap and Netcat are utilized by ethical hackers and penetration testers to identify and resolve security vulnerabilities and weaknesses. Nmap is an open-source command-line tool used for information gathering, network discovery, and security auditing. Whereas Netcat is a back-end tool that manages networks, monitors traffic flow between systems, as well as allows port scanning and listening. However, the plethora of tools and approaches available for these two phases often introduce inconsistencies and time wastage, which can lead to frustration and poor outcome for inexperienced penetration testers. Additionally, not all commands found online are relevant and applicable. In such situations, there is a high probability that the user will feel overwhelmed and exasperated with the overflow of new and foreign information. To address this daunting challenge, this study developed a methodical framework that can provide a technical guide for the reconnaissance and enumeration phases of the penetration testing lifecycle. Furthermore, a clear and thorough step-by-step procedure and detailed explanations of each stage and commands initiated using Nmap and Netcat are provided. The output of this study will be extremely beneficial and informative to a vast group of audience, ranging from university students majoring in security to individuals interested in ethical hacking, and even someone looking for a job with a position of a penetration tester. Furthermore, this technical guide on Nmap and Netcat extends the common body of knowledge in penetration, as a bridge between the industry and academia.