<p dir="ltr">The computational campaign reported in this thesis focuses on a series of experiments at Mach 2.85 carried out in the 1980s at NASA Ames Research Center on a set of cylinder / skewed flare configurations designed to produce highly three-dimensional shockwave / boundary-layer interactions in the absence of end-wall effects. Computations carried out in that era were unable to match the experimental results using the numerical techniques, turbulence models, and grid resolution available at the time. In the present work, newer Reynolds-averaged Navier-Stokes and detached eddy simulation methods have been applied to these flows, and relatively good agreement has been obtained with the experimental data. Difficulty in capturing the correct separation bubble size was encountered with initial detached eddy simulations, but the introduction of resolved turbulence via a boundary layer trip produced much better results. This thesis reports on results obtained for four inclination angles (0 deg, 5 deg, 10 deg, and 23 deg) of the skewed flare. Detached eddy simulation is seen to be an economical alternative to large eddy simulation for capturing many features of large-scale separation unsteadiness over long time intervals at true Reynolds number.</p>