This chapter examines the role of uncertainty, serendipity, and bureaucratic entanglement in shaping African migration trajectories through Latin America, focusing on the case of Mafara, a young man from Guinea who journeyed from West Africa to the U.S. via Brazil, Central America, and Mexico. Drawing on ethnographic encounters conducted between 2021 and 2025, the chapter conceptualizes migration as an assemblage of movements, interruptions, and encounters rather than a linear trajectory from origin to destination. It engages with theoretical perspectives that frame migration as turbulent trajectories, highlighting how mobility is sustained through improvisation, informal networks, and the ability to transform chance into opportunity. Serendipity—understood as the meeting point between preparedness and contingency—emerges as a structuring force within migrant lives, producing moments of both progress and vulnerability. The analysis situates Mafara’s experience within broader debates on im/mobility, youth migration, and the everyday politics of waiting, showing how migrants navigate systems of governance that thrive on uncertainty. Ultimately, the chapter argues that serendipity and bureaucracy operate not as opposites but as interdependent logics that co-produce contemporary migration through the Americas.