Many boulders on (101955) Bennu, a near-Earth rubble pile asteroid, show signs of in situ disaggregation and exfoliation, indicating that thermal fatigue plays an important role in its landscape evolution. Observations of particle ejections from its surface also show it to be an active asteroid, though the driving mechanism of these events is yet to be determined. Exfoliation has been shown to mobilize disaggregated particles in terrestrial environments, suggesting that it may be capable of ejecting material from Bennu’s surface. We investigate the nature of thermal fatigue on the asteroid, and the efficacy of fatigue-driven exfoliation as a mechanism for generating asteroid activity, by performing finite element modeling of stress fields induced in boulders from diurnal cycling. We develop a model to predict the spacing of exfoliation fractures, and the number and speed of particles that may be ejected during exfoliation events. We find that crack spacing ranges from ~1 mm to 10 cm and disaggregated particles have ejection speeds up to ~2 m/s. Exfoliation events are most likely to occur in the late afternoon. These predictions are consistent with observed ejection events at Bennu and indicate that thermal fatigue is a viable mechanism for driving asteroid activity. Crack propagation rates and ejection speeds are greatest at perihelion when the diurnal temperature variation is largest, suggesting that events should be more energetic and more frequent when closer to the Sun. Annual thermal stresses that arise in large boulders may influence the spacing of exfoliation cracks or frequency of ejection events.