Interface crack problems in graded orthotropic media are considered using analytical and computational techniques. In the analytical formulation an interface crack between a graded orthotropic coating and a homogeneous orthotropic substrate is considered. The principal axes of orthotropy are assumed to be parallel and perpendicular to the crack plane. Mechanical properties of the medium are assumed to be continuous with discontinuous derivatives at the interface. The problem is formulated in terms of the averaged constants of plane orthotropic elasticity and reduced to a pair of singular integral equations which are solved numerically to compute the mixed mode stress intensity factors and the energy release rate. In the second part of the study, enriched finite elements are formulated and implemented for graded orthotropic materials. Comparisons of the finite element and analytical results show that enriched finite element technique is capable of producing highly accurate results for crack problems in graded orthotropic media. Finally, periodic interface cracking and the four point bending test for graded orthotropic solids are modeled using enriched finite elements and the results are briefly discussed.