Cerebrospinal fluid leakage is an uncommon but significant complication of orbital and rarely lacrimal surgery which may have serious consequences including death. In a retrospective review of four orbital units, we report an incidence of cerebrospinal fluid leak (diagnosed intraoperatively) during exenteration, orbital decompression, and dacryocystorhinostomy of 1/154 (0.6%), 4/397 (1%), and 0/3,504 (0%), respectively. We found two additional cases of cerebrospinal fluid leaks associated with excision of orbital masses involving the orbital roof. In the literature, the incidence of cerebrospinal fluid leaks associated with orbital exenterations and decompressions was 1.6-16.7% and 0-10%, respectively. Cerebrospinal fluid leaks occur very rarely in dacryocystorhinostomies with only a few case reports found in the literature. Preventative measures, diagnosis, and management of this complication are discussed. Knowledge of anatomy and thorough preoperative assessment may predict areas at high risk for encountering cerebrospinal fluid leaks. Proper surgical technique further minimizes the risk for this complication. If a cerebrospinal fluid leak occurs, however, prompt diagnosis and management usually results in uncomplicated recovery.