The application of space syntax to the study of urban history—in this case, that of Tel Aviv and Jaffa (present-day Tel Aviv–Yafo)—can add a valuable, quantifiable component to the understanding of urban processes. However, it also demonstrates that historical spatio-syntactical analysis can prove misleading when interpreted separately from other types of historical evidence—for example, the ethnic conflicts that led to the formation of a strong divide between Tel Aviv and Jaffa despite their contiguous geography and interlaced street networks. A rigorous use of spatio-syntactic analysis in combination with “conventional” historical research methods can reveal the tensions and interplays between the spatio-physical and social forces that shape the life of cities, and it can invigorate our understanding of urban growth and transformationpatterns throughout history.