Did early Islamic Iran experience a process of dramatic urbanization, a general process that would finally culminate in the emergence (and eventual collapse) of several mega-cities in the wake of the Muslim conquests? While the hypothesis of a radical change of the urban landscape of early Islamic Iran seems to have been widely accepted, and several explanatory models have been offered, the evidence for an “urban revolution” of post-conquest Iran remains challenging. In the light of new archaeological evidence and re-readings of textual sources this paper critically reviews the evidence and methodologies that have been used to support the hypothesis of an early Islamic mega-urbanization. It then takes a closer look at two cities, Bukhara in Transoxiana and Darabgerd in Fars, weighing the archaeological and textual evidence against generalizing models of late antique and early Islamic urbanization. The complicated urban history of these two cities supports the impression of the first centuries of Islam as a period of experimentation framed in long-term developments, and it underscores the importance of taking regional and local factors and differences fully into account when studying the effects of the implementation of Muslim rule in Iran. As so often, taking the Muslim conquests as the beginning of something completely new, and completely different, may obscure rather than illuminate the broader picture. The hypothesis of a general dramatic urban growth strongly tied into the process of Islamization needs to be reconsidered and perhaps abandoned. Rather than a narrative of Islamic urbanization, the urban history of early Islamic Iran should rather be read as many stories of various and flexible adaptations of an already diverse urban landscape to a changing general framework. The paper will conclude with a brief outlook on how various narrative sources from the period of the transition from Sasanian to Muslim rule down to the Saljuq and even post-Mongol period may be used to gain a more differentiated picture of early Islamic Iran’s changing urban landscapes.