[Truncated abstract] The fracture of brittle materials in uniaxial compression is a complex process with the development of cracks generated from initial defects. The fracture mechanism and pattern of crack growth can be altered considerably by the presence of a free surface. In proximity of a free surface, initially stable cracks that require an increase in the load to maintain the crack growth can become unstable such that the crack growth maintains itself without requiring further increase in the load. This leads to a sudden relief of accumulated energy and, in some cases, to catastrophic failures. In the cases of rock and rock mass fracturing, this mechanism manifests itself as skin rockbursts and borehole breakouts or as various non-catastrophic forms of failure, e.g. spalling. Hence, the study of crack-boundary interaction is important in further understanding of such failures especially for the purpose of applications to resource engineering. Two major factors control the effect of the free boundary: the distance from the crack and the boundary shape. Both these factors as well as the effect of the initial defect and the material structure are investigated in this thesis. Three types of boundary shapes - rectilinear, convex and concave - are considered. Two types of initial defects - a circular pore and inclined shear cracks are investigated in homogeneous casting resin, microheterogeneous cement mixes and specially fabricated granulate material. The preexisting defects are artificially introduced in the physical model by the method of inclusion and are found to successfully replicate the feature of pre-existing defects in terms of load-deformation response to the applied external load. It is observed that the possibility of crack growth and the onset of unstable crack growth are affected by the type of initial defect, inclination of the initial crack, the boundary shape and the location of the initial defect with respect to the boundary. The initial defects are located at either the centre or edge of the sample. The stresses required for the wing crack initiation and the onset of unstable crack growth is highest for the initial cracks inclined at 35° to the compression axis, lowest at 45° and subsequently increases towards 60° for all the boundary shapes and crack locations. In the case of convex boundary, the stress of wing crack initiation and the stress of unstable crack growth are lower than for the case of rectilinear and concave boundary for all the crack inclinations and crack locations. The crack growth from a pre-existing crack in a sample with concave boundary is stable, requiring stress increase for each increment of crack growth. The stress of unstable crack growth for the crack situated at the edge of the boundary is lower than the crack located at the centre of the sample for all the crack inclinations and boundary shapes.