Pressure ridges are deformation features within the sea ice pack created through the collision of sea ice floes. Pressure ridges play an important role in ice drift and influence the mass and energy budgets of the Arctic Ocean. Over the past decade annual airborne surveys over Arctic sea ice have been conducted in late winter (March and April) by NASA’s Operation IceBridge (OIB) mission. A total of 74 OIB flights between 2010 and 2018 surveyed tens of thousands of kilometers of sea ice, providing observations of pressure ridges at a higher spatial and temporal resolution than previous airborne studies. Here we utilize Digital Mapping System (DMS) imagery to identify shadows cast by pressure ridge sails and, then, use these shadows to derive sail height. Over 64,000 DMS images were analyzed, allowing for more than 33 million individual sail height measurements to be calculated. We present the full sail-height distributions of new pressure ridges recently formed across a range of ice conditions on first-year (FYI) and multiyear ice (MYI), and we assess year-to-year variability. We find distinct characteristics depending on the ice type in which the pressure ridge formed. The mean and standard deviation of sail heights on FYI is ~20-30 cm lower than those formed on MYI. Maximum sail heights on FYI are ~1.5 m lower on average. Arctic sea ice is getting younger, shifting from predominantly MYI to predominantly FYI. Our results may inform new model parameterizations of pressure ridges on sea ice in the changing Arctic, thereby supporting advances in sea ice forecasting.