The near-surface characteristics of approximately 300 convective cold pools over the equatorial Indian Ocean are studied using surface meteorological variables from two equatorial Indian Ocean sites, radar imagery, and constrained cloud-resolving simulations. The observed temperature drop at cold pool onset is typically accompanied by a drying and a decrease in moist static energy, signifying air transport from above the boundary layer through precipitation-induced downdrafts. The decrease in the surface water vapor mixing ratio is more pronounced for stronger temperature drops. Composites reveal a slight enhancement in moisture coincident with a slight enhancement in temperature prior to the cold pool frontal temperature drop. The slight enhancements occur prior to a gust of increased surface winds, suggesting that the immediate cause is wind convergence. A statistical analysis combined with a focus on selected case studies is consistent with a view that the strongest cold pools occur in intermediate column water vapor paths with drier midtropospheres. Such conditions are more likely to occur during convectively suppressed phases of the Madden-Julian Oscillation, when cold pool mesoscale organization facilitates the ability of cumulus congestus to reach the middle troposphere. Cold pools thus help explain why tropical cumulus congestus are common. Cloud-resolving simulations capture realistic rain rates and surface wind changes (and thereby surface fluxes). The evolution in the model near-surface moisture field is unrealistic, however, with an erroneous moisture enhancement inside the cold pool edge that is attributed to rain evaporation. This supports a further focus on the model representation of cold pool frontal dynamics and mixing.Plain Language Summary Cold pools of air develop near the surface over the ocean when it rains. This colder air can move along the surface because it is denser and cause new raining clouds to form. They help modify the types of clouds and convection present over the tropical oceans, and their depiction in climate models may help improve climate model simulations of tropical climate. In this study we use observations of cold pools, combined with radar imagery, to confirm that cold pools are more pronounced when the middle of the atmosphere, between 2 and 5 km, is also drier. Cold pools, because they help support updrafts, can also help explain why seemingly isolated clouds reaching ∼5 km, are relatively common in the Tropics. Modeling simulations have instead focused on how anomalous moisture near the surface from previous convection, through, for example, rain evaporation, may spawn more convection. We find that in one cloud-resolving simulation, the rain evaporation is too much, leading to an unrealistic moisture distribution. This may explain why to date the understanding of cold pool processes through models and observations have not always agreed.