It is well known in the history of Spanish America that early colonial-era tributes in labor and commodities were gradually converted to tributes in cash, and tribute labor was gradually replaced by privately contracted labor. For Mexico and Central America, scholarship on these processes has remained largely separate from new, gendered histories. This article revisits tribute and native labor procurement, placing gender and family structure at the center of analysis. Focusing on Guatemala, the article argues that the transition from draft tribute labor to privately contracted labor increasingly drew entire families into migratory labor at Spanish agricultural enterprises. As out-migration from native communities lengthened from eight-day draft turns to longer “voluntary” stints, women and children began accompanying their men to colonial estates. Some women stayed behind, typically with small children, while their men left to earn wages. These women could face dire straits if their husbands died or did not return from abroad. Native women with absent husbands were likely to seek wages by migrating to the Spanish city. Further, the restructuring of labor within the cash economy may have encouraged parents to put their children out to work. Wages earned by native children sent to the city were usually remitted to the parents in the sending community, where tributes were collected. Contrary to popular stereotypes, the article concludes, women and children were at the vanguard of urbanization and hispanicization.