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Tropopause-overshooting convection in the midlatitudes provides a rapid transport pathway for air from the lower troposphere to reach the upper troposphere and lower stratosphere (UTLS) and can result in the formation of above-anvil cirrus plumes (AACPs) that significantly hydrate the stratosphere. Such UTLS composition changes alter the radiation budget and impact climate. Novel in situ observations from the NASA Dynamics and Chemistry of the Summer Stratosphere (DCOTSS) field campaign are used in this study to examine UTLS impacts from AACP-generating overshooting convection. Namely, a research flight on 31 May 2022 sampled active convection over the state of Oklahoma for more than 3 h with the NASA ER-2 high-altitude research aircraft. An AACP was bisected during this flight, providing the first such extensive in situ sampling of this phenomenon. The convective observations reveal pronounced changes in air mass composition and stratospheric hydration up to altitudes of 2.3 km above the tropopause and concentrations more than double background levels. Unique dynamic and trace gas signatures were found within the AACP, including enhanced vertical mixing near the AACP edge and a positive correlation between water vapor and ozone. Moreover, the water vapor enhancement within the AACP was found to be limited to the saturation mixing ratio of the low temperature overshoot and AACP air. Comparison with all remaining DCOTSS flights demonstrates that the 31 May 2022 flight had some of the largest tropospheric tracer and water vapor perturbations in the stratosphere and within the AACP.