Throughout history, vernacular architecture has sought to provide inhabitants with comfort, using local materials and techniques while drawing inspiration from the local culture. This goal has helped natural and passive environmental building techniques to emerge, evolve, and develop. Even though we are increasingly dependent on mechanical ventilation and cooling solutions, passive techniques are in favor due to global climate challenges and the drive toward sustainable construction. One of the most well-known passive cooling techniques is the windcatcher, or wind tower, as it is known in the Middle East (also known as a malqaf in Egypt). Windcatchers, which appeared in Egypt during the Pharaonic era, were also present in other vernacular Middle Eastern countries such as Iran and Iraq, and they differed in design and materials. This research aims to extract, analyze, and compare windcatchers throughout historical eras in Egypt and other Middle Eastern countries across three main eras: ancient, medieval, and modern. This study thus provides a timeline for developing these passive cooling systems, demonstrating how they were integrated into architecture over millennia. This study also investigates the design differences in these vernacular models, including their shapes, number of sides, and orientation, and correlates them to climatic and architectural conditions. The results highlight that the vernacular wind towers corresponded to the prevailing wind directions and the ventilation needs of the connected spaces. Furthermore, the findings question the effectiveness and appropriateness of some of the modern incorporations of wind towers, which borrow their design from local precedents.