Today, we look more in depth into NMAP, a popular open-source security scanner. We are interested in analyzing the accuracy of NMAP, as well as the network footprint seen when using some of its more popular scripts. To begin we create a network of six Virtual-Box machines which consist of three Metasploitable Linux, one Kali Linux, one Ubuntu 14.04, and one Centos 7 machines. We find the banner information gathered from a NMAP scan to be accurate if a machine’s security is not properly configured. Using Wireshark we analyze the amount of packets sent during a full version scan to be 182 KB over 123.54 seconds or 1.47 KB/sec. Next we use a Python program to exploit the Simple Mail Transfer Protocol (SMTP) to gather a list of known users on a server. We have success in validity emails on our Metasploitable virtual machine.