This research examines the environmental and storm-scale characteristics of the extreme rainfall and flooding in the Houston, Texas, area on 18 April 2016, known as the “Tax Day” flood. Radar and local mesonet rain gauge observations were used to identify the locations and structures of extreme rain-rate-producing cells, with special attention given to rotating updrafts. To supplement this observation-based analysis, a WRF-ARW simulation of the Tax Day storm in 2016 was examined for the influence of any attendant rotation on both the dynamics and microphysics of the cells producing the most intense short-term (i.e., subhourly to hourly) rainfall accumulations. Results show that the most intense rainfall accumulations in the model analysis, as in the observational analysis, are associated with rotating convective elements. A lowering of the updraft base, enhancement of the low-level vertical velocities, and increased low-level rainwater production is seen in rotating updrafts, compared to those without rotation. These differences are also maintained despite increased hydrometeor loading. The results agree with the findings of previous idealized model simulations that show dynamical accelerations associated with meso-γ-scale rotation can enhance convective rainfall rates.