This study conducted a comprehensive analysis of the Wi-Fi security at the National Institute of Transport in Dar es Salaam, Tanzania. The study used the experimental research design. The study involved testing a variety of devices, including 30 traditional Access Points and 10 smartphones, which can act as access points for other devices. The study utilized a total of 40 devices, selected through convenient sampling. Among these devices, 30 were traditional Access Points and 10 were smartphones acting as Access Points. The primary tool used in this study was a software called Instabridge, which was employed to collect information on wireless networks. The software gathered the names of the wireless networks for further analysis. The experimental process was divided into two main phases: Password extraction and Pairing of Devices. In the Password extraction phase, a smartphone equipped with the Instabridge software was used to collect information on the wireless network which are names and assessed the security of the passwords used. The software detected active devices offering wireless services and could easily unveil the passwords with a single click. In the Pairing of Devices phase, the passwords gathered from the wireless devices were used for authentication. The devices were successfully connected to the access points using the extracted passwords. The study indicated lack of proper security measures, with a significant majority of access points using unencrypted passwords for authentication. To address the existing shortcomings, respective recommendations were made.