This study uses gridded radar data to investigate the properties of deep convective storms that penetrate the tropical tropopause layer (TTL) and overshoot the cold-point tropopause during the Tropical Warm Pool-International Cloud Experiment (TWP-ICE). Overshooting convection during the observed break period is relatively more intense and exhibits lesser diurnal variability than severe monsoonal storms in terms of mean overshooting area in the TTL (as covered by >20 dBZ echoes). However, ground-based radar has geometrical constraints and sampling gaps at high altitude that lead to biases in the final radar product. Using synthetic observations derived from model-based data, ground-based radar is shown to underestimate the mean overshooting area in the TTL across both TWP-ICE regimes. Differences range from ∼180 km2 (∼100 km2 ) to ∼14 km2 (∼8 km2 ) between 14 and 18 km for the active (break) period. This implies that the radar is underestimating the transport of water and ice mass into the TTL by convective overshoots during TWP-ICE. The synthetic data is also used to correct profiles of the mean observed overshooting area. These are shown to differ only marginally between the two sampled regimes once the influence of a large mesoscale convective system, considered as a departure from normal monsoon behavior, was removed from the statistics. The results of our study provide a useful cross-validation comparison for satellite-based detections of overshooting top areas over Darwin, Australia.