This study is part of the efforts undertaken to resolve the “bad trough/good trough” issue for tropical cyclone (TC) intensity changes and to improve the prediction of these challenging events. Sensitivity experiments are run at 8-km resolution with vortex bogusing to extend the previous analysis of a real case of TC–trough interaction (Dora in 2007). The initial position and intensity of the TC are modified, leaving the trough unchanged to describe a realistic environment. Simulations are designed to analyze the sensitivity of TC prediction to both the variety of TC–trough configurations and the current uncertainty in model analysis of TC intensity and position. Results show that TC intensification under upper-level forcing is greater for stronger vortices. The timing and geometry of the interaction between the two cyclonic potential vorticity anomalies associated with the cutoff low and the TC also play a major role in storm intensification. The intensification rate increases when the TC (initially located 12° northwest of the trough) is displaced 1° closer. By allowing a gradual deformation and equatorward tilting of the trough, both scenarios foster an extended “inflow channel” of cyclonic vorticity at midlevels toward the vortex inner core. Conversely, unfavorable interaction is found for vortices displaced 3° or 4° east or northeast. Variations in environmental forcing relative to the reference simulation illustrate that the relationship between intensity change and the 850–200-hPa wind shear is not systematic and that the 200-hPa divergence, 335–350-K mean potential vorticity, or 200-hPa relative eddy momentum fluxes may be better predictors of TC intensification during TC–trough interactions.