Snakeskin-inspired surfaces generate direction-dependent interface strengths, with shearing in the cranial direction (i.e.; against the scales) generating greater strength than in the caudal one (i.e.; along the scales). This directionality is enabled by the transfer of load in friction and passive resistances. It is unclear if failure of these interfaces can be captured by models used for purely frictional interfaces. Interface shear tests complemented with particle image velocimetry (PIV) analyses were performed on snakeskin-inspired surfaces with different asperity geometries and on reference rough and smooth surfaces. The results of experiments performed at different initial effective stresses under constant normal stiffness boundary conditions show significant dilation-induced increases in effective stress. These increases were greater during cranial than caudal shearing, producing greater cranial strengths. These surfaces yielded nonlinear failure envelopes, with greater shear to effective stress ratios at smaller effective stresses, while the rough and smooth surfaces mobilized linear failure envelopes. The PIV analyses indicate that the snakeskin-inspired surfaces induce localized strains in the vicinity of the asperities, leading to wavy failure planes. The average shear strains are correlated with the mobilized shear strengths, with increases in effective stress leading to decreases in both strains and stress ratio.