Water vapor's contribution to Earth's radiative forcing is most sensitive to changes in its lower stratosphere concentration. One recognized pathway for rapid increases in stratospheric water vapor is tropopause-overshooting convection. Since this pathway has been rarely sampled, the NASA Dynamics and Chemistry of the Summer Stratosphere (DCOTSS) field project focused on obtaining in situ observations of stratospheric air recently affected by convection over the United States. This study reports on the extreme altitudes to which convective hydration was observed. The data show that the overworld stratosphere is routinely hydrated by convection and that past documented records of stratospheric heights of convective hydration were exceeded during several DCOTSS flights. The most extreme event sampled is highlighted, for which stratospheric water vapor was increased by up to 26% at an altitude of 19.25 km, a potential temperature of 463 K, and an ozone mixing ratio >1500 ppbv. Plain Language Summary When thunderstorms reach into the second layer of the atmosphere above Earth's surface, the stratosphere, they may impact the concentration and distribution of trace gases that are important to chemistry and climate. One gas that is routinely affected during these events is water vapor, which is typically scarce in the stratosphere. This study presents new aircraft observations of extreme heights in the stratosphere moistened by these thunderstorms. Since increases in stratospheric water vapor positively contribute to warming of Earth's climate and can activate chemistry that destroys ozone, better understanding of this phenomenon helps refine our understanding of its role in the climate system. The new aircraft observations provide clear evidence that water vapor is enhanced by thunderstorms at higher levels in the stratosphere than previously recognized.