Thermokarst lakes and basins are major components of ice-rich permafrost landscapes in East Siberian coastal lowlands and are regarded as indicators of regional climatic changes. We investigate the temporal and spatial dynamics of a 7.5 km2, partly drained thermokarst basin (alas) using field investigations, remote sensing, Geographic Information Systems (GIS), and sediment analyses. The evolution of the thermokarst basin proceeded in two phases. The first phase started at the Pleistocene/Holocene transition (13 to 12 ka BP) with the initiation of a primary thermokarst lake on the Ice Complex surface. The lake expanded and persisted throughout the early Holocene before it drained abruptly about 5.7 ka BP, thereby creating a > 20 m deep alas with residual lakes. The second phase (5.7 ka BP to present) is characterized by alternating stages of lower and higher thermokarst intensity within the alas that were mainly controlled by local hydrological and relief conditions and accompanied by permafrost aggradation and degradation. It included diverse concurrent processes like lake expansion and stepwise drainage, polygonal ice-wedge growth, and the formation of drainage channels and a pingo, which occurred in different parts of the alas. This more dynamic thermokarst evolution resulted in a complex modern thermokarst landscape. However, on the regional scale, the changes during the second evolutionary phase after drainage of the initial thermokarst lakes were less intense than the early Holocene extensive thermokarst development in East Siberian coastal lowlands as a result of a significant regional change to warmer and wetter climate conditions.