This paper focuses on how virtual objects’ shadows as well as differences in alignment between virtual and real lighting influence distance perception in optical see-through (OST) augmented reality (AR). Four hypotheses are proposed: (H1) Participants underestimate distances in OST AR; (H2) Virtual objects’ shadows improve distance judgment accuracy in OST AR; (H3) Shadows with different realism levels have different influence on distance perception in OST AR; (H4) Different levels of lighting misalignment between real and virtual lights have different influence on distance perception in OST AR scenes. Two experiments were designed with an OST head mounted display (HMD), the Microsoft HoloLens. Participants had to match the position of a virtual object displayed in the OST-HMD with a real target. Distance judgment accuracy was recorded under the different shadows and lighting conditions. The results validate hypotheses H2 and H4 but surprisingly showed no impact of the shape of virtual shadows on distance judgment accuracy thus rejecting hypothesis H3. Regarding hypothesis H1, we detected a trend toward underestimation; given the high variance of the data, more experiments are needed to confirm this result. Moreover, the study also reveals that perceived distance errors and completion time of trials increase along with targets’ distance.