Cloud models show that precipitation is more likely to occur in larger shallow clouds and/or in an environment with more moisture, in part as a result of decreasing the impacts of entrainment mixing on the updrafts. However, the role of cloud size in shallow cloud precipitation onset from global satellite observations has mostly been examined with precipitation proxies from imagers and has not been systematically examined in active sensors, primarily because of sensitivity limitations of previous spaceborne active instruments. Here we use the more sensitive CloudSat/CALIPSO observations to identify and characterize the properties of individual contiguous shallow cumulus cloud objects. The objects are conditionally sampled by cloud-top height to determine the changes in precipitation likelihood with increasing cloud size and column water vapor. On average, raining shallow cumulus clouds are typically taller by a factor of 2 and have a greater horizontal extent than their nonraining counterparts. Results show that for a fixed cloud-top height the likelihood of precipitation increases with increasing cloud size and generally follows a double power-law distribution. This suggests that the smallest cloud objects are able to grow freely within the boundary layer but the largest cloud objects are limited by environmental moisture. This is supported by our results showing that, for a fixed cloud-top height and cloud size, the precipitation likelihood also increases as environmental moisture increases. These results are consistent with the hypothesis that larger clouds occurring in a wetter environment may be better able to protect their updrafts from entrainment effects, increasing their chances of raining.