The following paper presents the results of radiocarbon (14C) dating of Middle Bronze Age (MB) contexts in Jerusalem. The dates, sampled with microarchaeology methods from three different locations along the eastern slopes of the city’s ancient core, reveal that Jerusalem was initially settled in the early phases of the period, with public architecture first appearing in the beginning of the 19th century BC and continued to develop until the 17th century BC. At that time, a curious gap in settlement is noted until the 16th century BC, when the site is resettled. The construction of this phase continued into the early 15th century BC. The dates presented are discussed in both the site-level, as well as their far-reaching implications regarding MB regional chronology. It is suggested here that the high chronology, dating the Middle Bronze Age between 2000 and 1600 BC is difficult to reconcile with dates from many sites. In contrast, a more localized chronology should be adopted, with the Middle Bronze Age continuing into the early 15th century BC in certain parts of the southern Levant, such as the region of Jerusalem.