At the end of the 19th century the state of Yucatan became a monocrop economy centered around the export of twine made from the henequen agave. The regions old haciendas were transformed into proto-industrial units where henequen was cultivated and processed. The new hacienda system brought about the invention and adoption of machinery used in henequen production as well as the proliferation of debt peonage, a coercive labor arrangement in which peasants become indebted to the landlord and must in turn offer their labor to him until their loans are repayed. I argue that this was the case because the introduction of machines brought along higher returns to experience, and this in turn generated greater incentives for landlords to retain (skilled) workers in their control. I then formalize this theory in a mathematical model. Finally, with data from a particular hacienda, I show that, empirically, 1) experienced operators of the machines produced higher outputs and 2) the possibility of learning-by-doing shifted demand for coerced labor.