Livelihoods approaches focus on the poor and their knowledge and agency, but risk underplaying broader contextual forces which constrain and shape that agency. Livelihood trajectories approaches attend more fully to these structural, contextual dynamics. A three‐year study using quantitative and qualitative methods investigated livelihood trajectories over two decades in a village affected by deforestation in Northeast Cambodia, and sought to identify critical junctures structuring those trajectories. A timber rush, a land rush, a turn to agriculture and ongoing competition to shape post‐forest reterritorialisation were identified as the critical junctures. These transformed the physical environment, and initiated waves of migration which in turn transformed the social and economic structure and everyday life of the village. This valuably disrupts narrative simplifications associated with community forestry. The junctures furthermore suggest an analytical framework for understanding deforestation‐livelihoods dynamics in other contexts, thus demonstrating how livelihood trajectories research might contribute to middle‐level theory building.