In addressing the question of how and why Indigenous people initiated diverse kinds of engagements with colonial agents, this chapter highlights two crucial variables that should be considered in any archaeological investigation of colonialism. One concerns Indigenous sociopolitical and economic organizations, including dimensions such as polity size, polity structure, landscape management practices, and regional sociopolitical relationships. The other involves the various permutations of colonial programs that encroached on tribal lands, as exemplified by managerial, missionary, and settler colonies. A significant challenge in the study of colonialism is that Indigenous people did not encounter one type of colonial program over time but rather a plethora of colonial agents with divergent policies and practices. This chapter argues for archaeological investigations of colonialism that take a long-term perspective in examining the full range of colonial succession patterns that unfolded in tribal lands and how Native people created innovative strategies for mitigating colonialism and making the most of new technologies, trade connections, settlement arrangements, and economic opportunities. The chapter concludes with several examples of resourceful pathways that Native people initiated in their entanglements with colonial agents.