The frictional behavior of soil-construction material interfaces is of significant importance in geotechnical engineering applications such as retaining structures, pile foundations, geosynthetic liners, and trenchless technologies. Since most failures initiate and develop on the interfaces, special attention is required to predict the capacity of these weak planes in the particular application. Pipe-jacking and microtunneling technologies are being more widely used over the past decade and there is significant interest to predict the jacking forces and jacking distances achievable in order to achieve more efficient design and construction. This study focuses on the evaluation of the frictional characteristics and factors affecting the shear strength of pipe-soil interfaces. Eight different pipes made from fiber reinforced polymer (FRP), polycrete, steel, concrete, and vitrified clay were tested in the experimental program. For this purpose, a new apparatus was designed to conduct conventional interface direct shear testing on pipes of different curvature. This device allows coupons cut from actual conduits and pipes to be tested in the laboratory under controlled conditions. The apparatus includes a double-wall shear box, the inner wall of which is interchangeable to allow for testing against surfaces of different curvatures. By considering a narrow width section, the circular interface of pipes was approximated with a surface along the axial direction and the boundary is defined by the inner box. Roughness tests were performed using a stylus profilometer to quantify the surface characteristics of the individual pipes and relate these to the interface shear behavior. The surface topography showed different degrees of variability for the different pipes. To extend the range of roughness values tested and force the failure to occur in the particulate media adjacent to the interface, two artificial pipe surfaces were created using rough sandpapers. Interface shear tests were performed using the new apparatus with air-pluviated dense specimens of Ottawa 20/30 sand. Additional tests were performed using Atlanta blasting sand to evaluate the effect of particle angularity. The effect of normal stress and relative density were also examined. The interface strength was shown to increase with surface roughness and finally reach a constant value above a certain critical roughness value, which corresponded to the internal strength of the soil itself. This represented the failure location moving from the interface into the soil adjacent to the interface. Both the strength and the shearing mechanism were thus affected by the surface topography. It was also shown that the interface shear strength was affected by particle angularity, relative density and normal stress.