Although often associated with colonial times, tropical plantations growing industrial crops such as rubber, sugar, and oil palm are once again expanding. They employ hundreds of thousands of workers, who still use remarkably basic tools. Flagging colonial continuities, labor activists campaign against the reemergence of unfree labor and “modern forms of slavery.” Paradoxically, labor activists also highlight the opposite problem: the casualization of plantation work, as workers are hired daily and fired at will. Recognizing that both “free” and unfree labor regimes have a long history in Indonesia, and plantations have pivoted between these modes more than once, my study compares plantation labor regimes in the colonial, New Order, and “reform” periods (post-1998) to answer three questions. First, given that employers always want to access disciplined labor at the lowest possible price, what were the conditions that led employers to rely on unfree labor in some cases, and “free” labor in others? Second, to what extent was unfreedom imposed as a response to excessive freedom among workers and peasants? Third, how were the costs of social reproduction distributed between workers and employers, and what pressures from workers or regulators (state, colonial, transnational) affected this distribution? In addition to published sources, I draw on my ethnographic research in West Kalimantan (2010–2015) to explore contemporary experiences of un/freedom among workers on state and private oil palm plantations.