The stability of wells drilled into bedded formations, e.g., shales, depends on the orientation between the bedding and the borehole axis. If the borehole is drilled sub-parallel to bedding, the risk of borehole instabilities increases significantly. In this study, we examined the formation of stress-induced borehole breakouts in Posidonia shale by performing a series of thick-walled hollow cylinder experiments with varying orientations of the bedding plane with respect to the borehole axis. The thickwalled hollow cylinders (40 mm in diameter and 80 mm in length containing an 8 mm diameter borehole) were loaded isostatically until formation of breakouts. The onset of borehole breakout development was determined by means of acoustic emission activity, strain measurements, ultrasonic velocities and amplitudes. The critical pressure for breakout initiation decreased from 151 MPa by approximately 65 % as the bedding plane inclination changed from normal to parallel to the borehole axis. The finely bedded structure in the shale resulted in an anisotropy in elasticity and strength from which the variation in strength dominated the integrity of the thick-walled hollow cylinders.