This is a retrospective study of the frequency and factors that portend enophthalmos following orbital osteotomies and transposition for craniofacial malformations. Clinically obvious postoperative enophthalmos (POE) was noted in 23 (37.7 percent) of 61 patients undergoing such procedures. Postoperative enophthalmos was observed in 86 percent of Apert patients who had combined anteromedial orbital transposition and in 48 percent of patients with hypertelorbitism who had standard 360-degree osteotomies. In contrast, the incidence of postoperative enophthalmos was 21 percent following frontofacial (monobloc) or subcranial (Le Fort III) advancement. Postoperative enophthalmos also correlated with the occurrence of orbital fracture/fragmentation and with disruption of the periorbita. This study underscores the importance of establishing the correct relationship of the globe to the orbital rim (euophthalmos) while maintaining the spatial position of the eye, especially its anterior projection. Postoperative enophthalmos can be prevented by inserting bone grafts into orbital osteotomy gaps, correcting orbital volume/morphology following floor or wall outfracture/fragmentation, and preserving the periorbital supporting system.