A major theme in the social and economic history of the Ottoman Empire has been the permeable nature of social and occupational boundaries, especially as it was observed from the seventeenth to nineteenth centuries. Professional soldiers, who as a rule were members of the elite askeri service class, frequently established livelihoods in trade or the crafts in towns where they were assigned, in order to supplement their income, while artisans and merchants obtained nominal memberships in the same military units, often to secure the legal and tax privileges of the askeri class. The growing presence of soldiers throughout the empire, whether nominal or real, has led some historians to describe Ottoman society as undergoing “militarization,” or more generally, “askerization.” Studies of this complex process have tended to outline its general features and offer a broad, usually quantitative demographic analysis. The present study aims to complement this emphasis with an in-depth, micro-historical focus on the households of three Ottoman military officers active in seventeenth-century Aleppo. It draws on scores of local, Arabic-language manuscript records, primarily the registers of the local law court (sijillat), and Ottoman Turkish-language imperial records, mostly cadastral documents (tahrirs) and administrative correspondence from the central administration in Istanbul. The study reconstructs key practices that enabled military cadres to establish themselves as major players in the provincial society and economy: the acquisition of clients and slaves, the building of manor houses in strategic locations, the founding of charitable foundations (waqfs), but most important of all, the extension of moneylending and investment operations throughout the city and countryside. Represented in this selection of households are (1) members of the locally garrisoned imperial herald unit (chavushan); (2) cavalry officers (sipahis) administering land assignments (timars); and (3) persons descending from pashas and vassal lords (muteferrika). Particular attention will be paid to the varying strategies by which each household, over time, brought both villagers and townspeople into relations of financial dependence and consolidated their position through the geographical clustering of residences and/or the foundation of waqfs. The assertion by these households of economic and social influence in the second half of the seventeenth century sets an early precedent for the ascendancy of the landed urban notables in the eighteenth and nineteenth centuries.