A three-dimensional cloud-resolving model is used to simulate the transport of boundary layer tracers into the lower stratosphere via midlatitude supercells. We analyze three cases: a single tropopause, a weak inversion double tropopause, and a strong inversion double tropopause. Preliminary results show differences in mass aloft during the mature stage of the storm, but only minor differences in irreversible transport. Further, chemical plumes and tropopause structures are investigated using aircraft observations from both the NASA MACPEX and SEAC4RS missions. Enhanced carbon monoxide plumes are identified from in situ vertical profiles, and back trajectories and observations of precipitation are used to verify which parcels were influenced by recent convection. The tropopause structure in the vicinity of each plume is then categorized using aircraft data. Preliminary results show the majority of analyzed plumes show double tropopause structures, but only double tropopause structures with weak inversions show increases in plume penetration depth.