Tropopause polar vortices (TPVs) are long-lived, coherent vortices based on the dynamic tropopause and characterized by potential vorticity anomalies. TPVs exist primarily in the Arctic with potential impacts ranging from surface cyclone generation and Rossby wave interactions to dynamic changes in sea ice. While previous analyses have focused on model output indicating the importance of clear-sky and cloud-top radiative cooling in the maintenance and evolution of TPVs, no studies have focused on local observations to confirm or deny these results. This study uses cloud and atmospheric state observations from Summit Station, Greenland, combined with single column experiments using the Rapid Radiative Transfer Model to investigate the effects of clear-sky, ice-only, and all-sky radiative cooling on TPV intensification. The ground-based observing system combined with temperature and humidity profiles from the European Centre for Medium-Range Weather Forecasts’ fifth Reanalysis dataset, which assimilates the twice-daily soundings launched at Summit, provides novel details of local characteristics of TPVs. Longwave radiative contributions to TPV diabatic intensity changes are analyzed with these resources, starting with a case study focusing on observed cloud properties and associated radiative effects, followed by a composite study used to evaluate observed results alongside previously simulated results. Stronger vs. weaker vertical gradients in anomalous clear-sky radiative heating rates, contributing to Ertel potential vorticity changes, are associated with strengthening vs. weakening TPVs. Results show that clouds are sometimes influential in the intensification of a TPV, and composite results share many similarities to modeling studies in terms of atmospheric state and radiative structure.