We present a new approach to categorizing different types of urban development, namely infilling, fringe, and leapfrogging, based on construction projects as the fundamental unit of analysis. We focus on the role of the leapfrogging projects as seeds for new developments, leading to urban sprawl extending beyond statutory plans. To examine this phenomenon, we analyze the 50-year growth of three major Israeli cities: Netanya, Haifa, and Safed and the 5-year dynamics of 66 cities in Israel that account for 68% of the country’s population. Our investigation utilizes extensive databases of Israeli development plans, along with high-resolution aerial photographs covering the investigated areas and time periods. These datasets were supplemented by detailed Israeli databases encompassing roads, buildings, and other infrastructure elements, compiled by the Israeli Mapping Centre for the year 2018. Our analysis reveals that although most construction projects in Israel adhere to land-use plans, urban sprawl in Israel remains highly unpredictable. Leapfrogging is specific in terms of both place and time, attracts additional development nearby, and forces the divergence from development plans. We conclude that urban modelers’ view of urban dynamics being driven by common and systematic forces, is unrealistic. Instead, every city has its specific and self-enforcing development drivers that define its land-use dynamics. This explains the limited success of the Cellular Automata (CA) models in explaining and predicting urban dynamics.