The rapid deployment of wireless networks, combined with an increasing demand for performance and security, resulted in the significant evolution of standards. Today, ) and Wi-Fi Protected Access 3 (WPA3) are the latest standard and set of security protocols. In order to enhance the security protections offered by these networks, it remains key to adopt the newest standards and promptly deprecate any old and vulnerable protocols. With this perspective, and the knowledge that early research in new protocols allows us to identify and address shortcomings before they are widely-adopted in practice, we are motivated to perform rigorous security and privacy analyses.In this dissertation, we perform an extensive wireless survey to understand and contextualize the Wi-Fi (IEEE 802.11) landscape. It allows us to gain real-world insights in the adoption rates of deprecated, recommended, and state-of-the-art protocols, and thereby identify trends and determine their security impact in practice. Based on our newfound insights, we perform a security and privacy analysis on the Temporal Key Integrity Protocol (TKIP) and Wi-Fi Fine Timing Measurement (FTM), revealing a wide-variety of sidechannels and security vulnerabilities. In order to ease and streamline our research process, and address implementation challenges faced throughout, we design a novel framework for rapid prototyping. Our framework allows one to rapidly test hypothesis on new weaknesses, implement proof-of-concepts, build on-target fuzz-testing tools, create testing suites (e.g., test if a device is vulnerable to known attacks), and automate experiments. We then demonstrate the features of our framework by means of two practical use cases. First, we perform a security analysis on the Wi-Fi Management Frame Protection (MFP) standard and its implementations, revealing numerous deauthentication vulnerabilities. Second, we analyze frame queuing mechanisms used within access points, revealing vulnerabilities which enable an adversary to bypass encryption. Finally, we release our framework for rapid prototyping to the community in order to encourage and support further security and privacy research.