We present a series of gasdynamical simulations of the interaction of a dense, cool interstellar cloud with a high-speed, supersonic wind that confines and accelerates the embedded cloud. Our goal is to attempt to determine if such clouds can survive various potentially disruptive instabilities, that occur at their peripheries, long enough to be accelerated to speeds which are comparable to the wind velocity. These simulations are performed using two-dimensional, Eulerian gas dynamics on both an axisymmetric (about the cloud axis) and 'slab' geometric grid. The spatial and temporal resolutions of the simulations are varied over a wide range to investigate the effects of small-scale instabilities on the overall acceleration of clouds and the development of large-scale, disruptive instabilities. Also, we study the effects of wind/cloud Mach number variations by changing the wind speed constant at about 12 km/s (which corresponds to a cloud temperature of 10,000 K). The current simulations track the evolution of clouds as they are accelerated to speeds approximately 4-5 times greater than their internal sound speeds. Furthermore, the models with the highest resolution were extended far beyond quasi-linear Rayleigh-Taylor growth times reaching 6-7 Rayleigh-Taylor growth times for the largest scale instabilities before being terminated because of the accumulation of errors at the rear grid boundary.