A ubiquitous cold signal near the tropopause, here called “tropopause layer cooling” (TLC), has been documented in deep convective regions such as tropical cyclones (TCs). Temperature retrievals from the Constellation Observing System for Meteorology, Ionosphere, and Climate (COSMIC) reveal cooling of order 0.1–1 K day−1 on spatial scales of order 1000 km above TCs. Data from the Cloud Profiling Radar (onboard CloudSat) and from the Cloud–Aerosol Lidar with Orthogonal Polarization [onboard the Cloud–Aerosol Lidar and Infrared Pathfinder Satellite Observations (CALIPSO)] are used to analyze cloud distributions associated with TCs. Evidence is found that convective clouds within TCs reach the upper part of the tropical tropopause layer (TTL) more frequently than do convective clouds outside TCs, raising the possibility that convective clouds within TCs and associated cirrus clouds modulate TLC. The contribution of clouds to radiative heating rates is then quantified using the CloudSat and CALIPSO datasets: in the lower TTL (below the tropopause), clouds produce longwave cooling of order 0.1–1 K day−1 inside the TC main convective region, and longwave warming of order 0.01–0.1 K day−1 outside; in the upper TTL (near and above the tropopause), clouds produce longwave cooling of the same order as TLC inside the TC main convective region, and one order of magnitude smaller outside. Considering that clouds also produce shortwave warming, cloud radiative effects are suggested to explain only modest amounts of TLC while other processes must provide the remaining cooling.