The importance of loading and unloading procedures has been shown in a variety of different methods for biological dry adhesives, such as the fibers on the feet of the Tokay gecko, but biomimetic dry adhesives have yet to be explored in a similar manner. To date, little work has systematically varied multiple parameters to discern the influence of the testing procedure, and the effect of the approach angle remains uncertain. In this study, a synthetic adhesive is moved in 13 individual approach and retraction angles relative to a flat substrate as well as 9 different shear lengths to discern how loading and unloading procedures influence the preload, adhesion, and shear/friction forces supported. The synthetic adhesive, composed of vertical 10 μm diameter semicircular poly(dimethylsiloxane) fibers, is tested against a 4 mm diameter flat glass puck on a home-built microtribometer using both vertical approach and retraction tests and angled approach and retraction tests. The results show that near maximum adhesion and friction can be obtained for most approach and retraction angles, provided that a sufficient shear length is performed. The results also show that the reaction forces during adhesive placement can be significantly reduced by using specific approach angles, resulting for the vertical fibers in a 38-fold increase in the ratio of adhesion force to preload force, μ′, when compared to that when using a vertical approach. These results can be of use to those currently researching gecko-inspired adhesives when designing their testing procedures and control algorithms for climbing and perching robots.