Tablets of amorphous sucrose and sucrosepolyvinylpyrrolidone (PVP) amorphous solid dispersions were compressed at 25, 75, or 150 MPa at dwell times ranging from 5 to 900 s. Compression-induced physical destabilization was evident from differential scanning calorimetry. Crystallization kinetics was monitored using a laboratory source X-ray diffractometer, while crystallization was detected using highly sensitive synchrotron radiation. At the highest compression pressure, sucrose crystallization was evident immediately after compression. However, the addition of PVP, even at a low concentration of 1% w/w, inhibited crystallization. Furthermore, nucleation itself was completely prevented at higher PVP concentrations (≥15% w/w) under a compression pressure of practical interest (150 MPa with 5 s dwell time). However, an increase in dwell time (e.g., to 60 s) facilitated nucleation, and there was an increase in nucleation density as a function of dwell time. Both polymer content and sample history were pivotal factors limiting compression-induced crystallization in plasticized amorphous systems. Generally, plasticization was found to amplify compression-induced destabilization. PVP, in a concentration dependent manner, attenuated this effect.