A number of impending and actual pit wall failures have been observed and documented which have been interpreted to initiate on newly generated structural features. This infers failure through intact rock. Failure mechanisms have been postulated resulting from circumferential stress, extensional strain and brittle flexure. These will be discussed in the context of the failures and the associated monitoring. The implications of failure initiating on “unknown” features has a significant impact for deep open pit mines where designs are based on the expected structural regime. Being able to anticipate such failures is important for design. Equally important is management of such changes as they arise. In this context, monitoring using high resolution microseismic techniques will be discussed as a means of providing early warning of such failures.