Spaceborne lidar observations from the Cloud–Aerosol Lidar and Infrared Pathfinder Satellite Observations (CALIPSO) satellite provide the first-ever observations of cloud vertical structure and phase over the entire Greenland Ice Sheet. This study leverages CALIPSO observations over Greenland to pursue two investigations. First, the GCM-Oriented CALIPSO Cloud Product (CALIPSO-GOCCP) observations are compared with collocated ground-based radar and lidar observations at Summit, Greenland. The liquid cloud cover agrees well between the spaceborne and ground-based observations. In contrast, ground–satellite differences reach 30% in total cloud cover and 40% in cloud fraction below 2 km above ground level, due to optically very thin ice clouds (IWC < 2.5 × 10−3 g m−3) missed by CALIPSO-GOCCP. Those results are compared with satellite cloud climatologies from the GEWEX cloud assessment. Most passive sensors detect fewer clouds than CALIPSO-GOCCP and the Summit ground observations, due to different detection methods. Second, the distribution of clouds over the Greenland is analyzed using CALIPSO-GOCCP. Central Greenland is the cloudiest area in summer, at +7% and +4% above the Greenland-wide average for total and liquid cloud cover, respectively. Southern Greenland contains free-tropospheric thin ice clouds in all seasons and liquid clouds in summer. In northern Greenland, fewer ice clouds are detected than in other areas, but the liquid cloud cover seasonal cycle in that region drives the total Greenland cloud annual variability with a maximum in summer. In 2010 and 2012, large ice-sheet melting events have a positive liquid cloud cover anomaly (from +1% to +2%). In contrast, fewer clouds (−7%) are observed during low ice-sheet melt years (e.g., 2009).