The NASA ER-2 aircraft sampled the lower stratosphere over North America during the field mission for the NASA Studies of Emissions and Atmospheric Composition, Clouds and Climate Coupling by Regional Surveys (SEAC4 RS). This study reports observations of convectively influenced air parcels with enhanced water vapor in the overworld stratosphere over the summertime continental United States and investigates three case studies in detail. Water vapor mixing ratios greater than 10 ppmv, which is much higher than the background 4 to 6 ppmv of the overworld stratosphere, were measured by the JPL Laser Hygrometer (JLH Mark2) at altitudes between 16.0 and 17.5 km (potential temperatures of approximately 380 to 410 K). Overshooting cloud tops (OTs) are identified from a SEAC4 RS OT detection product based on satellite infrared window channel brightness temperature gradients. Through trajectory analysis, we make the connection between these in situ water measurements and OT. Back trajectory analysis ties enhanced water to OT 1 to 7 days prior to the intercept by the aircraft. The trajectory paths are dominated by the North American monsoon (NAM) anticyclonic circulation. This connection suggests that ice is convectively transported to the overworld stratosphere in OT events and subsequently sublimated; such events may irreversibly enhance stratospheric water vapor in the summer over Mexico and the United States. A regional context is provided by water observations from the Aura Microwave Limb Sounder (MLS).