Orbital exenteration is an operation most commonly carried out as part of a craniofacial section for malignant tumors of the skull base when there is orbital invasion by the tumor. Indications for orbital exenteration in isolation are uncommon. These include malignant tumors arising from the globe or adnexal structures such as the periorbita, conjuctiva, lacrimal gland, lacrimal sac and nasolacrimal duct system. Tumors of the lacrimal sac are very rare and treatment is dependent upon pathology. This may consist of surgery, radiotherapy, chemotherapy or a combination of these modalities. We present a case of high grade mucoepidemoid carcinoma of the lacrimal sac in a 62 year old man. The optimum treatment for this is wide surgical resection with clear margins. The patient initially presented with epiphora due to obstruction of the nasolacrimal duct system. Examination showed displacement of the left eye laterally and in a cephalad direction. Extraocular eye movements were restricted with diplopia on lateral gaze, inferior gaze and superior gaze. CT scan showed a mass occupying the lower medial quadrant of the left orbit invading the skin of the medial aspect of the lower eyelid. The tumor extended to involve the subcutaneous soft tissues overlying the nasal bone and extended up to the lamina papyracea of the left orbit. The patient was managed by orbital exenteration with en bloc resection of the lacrimal fossa. Following removal of the orbital contents and lacrimal fossa the defect was reconstructed using a split thickness skin graft to line the orbital bone. After healing an orbital prosthesis was fabricated to provide esthetic rehabilitation. The operative procedure for this uncommon operation are described in detail in the video.