Pillars are any structures left between two or more underground openings. The stability of pillars is normally considered to depend on shape (defined by width to height ratio), rock mass strength, extraction ratio, in situ stresses and the gross structural features (i.e. joints, contacts, faults etc). Recent experience has shown that pillar stability is also controlled by the relative orientation of the orebody with respect to the in situ principal stress. In inclined orebodies, pillars are loaded in compression and shear, thus creating unsymmetrical stress distribution. Failure mechanisms of these pillars are little known. This paper investigates the failure mechanisms of pillars under shear loading. Two dimensional elastic numerical modeling was used to examine the behavior of pillars in different orebody inclinations relative to the major farfield stress orientation. First, the paper reviews pillar design approaches including the empirical pillar design chart and uses numerical modeling to investigate the effect of the major farfield stress orientation on pillar stability. It is concluded that the empirical pillar design chart be used with caution, and that for orebodies under shear loading mine planning and design should take this into consideration since such geometrical orebody/stress relations put mine structures at higher risk of instability.