Abstract: Pleistocene water crossings, long thought to be an innovation of Homo sapiens, may extend beyond our species to encompass Middle and Early Pleistocene Homo. However, it remains unclear how water crossings differed among hominin populations, the extent to which Homo sapiens are uniquely flexible in these adaptive behaviors, and how the tempo and scale of water crossings played out in different regions. I apply the adaptive flexibility hypothesis, derived from cognitive ecology, to model the global data and address these questions. Water-crossing behaviors appear to have emerged among different regional hominin populations in similar ecologies, initially representing nonstrategic range expansion. However, an increasing readiness to form connections with novel environments allowed some H. sapiens populations to eventually push water crossings to new extremes, moving out of sight of land, making return crossings to maintain social ties and build viable founder populations, and dramatically shifting subsistence and lithic provisioning strategies to meet the challenges of variable ecological settings.