Changes in Greenland's marine-terminating outlet glaciers have led to changes in the flux of icebergs into Greenland's coastal waters, yet icebergs remain a relatively understudied component of the ice-ocean system. We developed a simple iceberg delineation algorithm for Landsat imagery. A machine learning-based cloud mask incorporated into the algorithm enables us to extract iceberg size distributions from open water even in partially cloudy scenes. We applied the algorithm to the Landsat archive covering Disko Bay, West Greenland, to derive a time series of iceberg size distributions from 2000–02 and 2013–15. The time series captures a change in iceberg size distributions, which we interpret as a result of changes in the calving regime of the parent glacier, Sermeq Kujalleq (Jakobshavn Isbræ). The change in calving style associated with the disintegration and disappearance of Sermeq Kujalleq's floating ice tongue resulted in the production of more small icebergs. The increased number of small icebergs resulted in increasingly negative power law slopes fit to iceberg size distributions in Disko Bay, suggesting that iceberg size distribution time series provide useful insights into changes in calving dynamics.