Patients afflicted with retinoblastoma or other malignant orbital tumors often undergo eyeball excision and irradiation in infancy, which results in severe deformities of the orbit. It is very difficult to achieve the reconstruction of such severely depressed and contracted eye sockets because both augmentation and formation of an eye socket are required. We usually perform a free-flap transfer with microvascular anastomoses in such situations and have experienced 25 cases since 1980. Various kinds of flaps, such as the groin flap, dorsalis pedis flap, scapular flap, and others, were utilized. The degree of depression and whether sufficient conjunctiva for lining of the eye socket remains are important in the selection and design of the donor flap. To obtain an orbit with a natural appearance, many of the patients required subsequent minor revision operations such as debulking, dermal fat grafts, canthoplasty, fascia suspension, and so on.