The IEEE 802.11 standard for wireless local area networking (WLAN), commercially known as Wi-Fi, has become a necessity in our day-to-day life. Over a billion Wi-Fi access points connect close to hundred billion of IoT devices, smart phones, tablets, laptops, desktops, smart TVs, video cameras, monitors, printers, and other consumer devices to the Internet to enable millions of applications to reach everyone, everywhere. The evolution of Wi-Fi technology also resulted in the first commercial piloting of spread spectrum, high speed optical communications, OFDM, MIMO and mmWave pulse transmission technologies, which then became more broadly adopted by cellular phone and wireless sensor networking industries. The popularity and widespread Wi-Fi deployment in indoor areas further motivated innovation in opportunistic cyberspace applications that exploit the ubiquitous Wi-Fi signals. The RF signal radiated from Wi-Fi access points creates an “RF cloud” accessible to any Wi-Fi equipped device hosting or supporting these opportunistic applications. Wi-Fi positioning and location intelligence were the first popular opportunistic applications of Wi-Fi’s RF cloud. Today, researchers are investigating opportunistic applications of Wi-Fi signals for gesture and motion detection as well as authentication and security. This paper provides a holistic overview of the evolution of Wi-Fi technology and its applications as the authors experienced it in the last few decades.