Epstein-Barr virus is a known cause of dacryoadenitis that is typically sensitive to corticosteroid treatment. When affecting the orbit, particularly the lacrimal gland, Epstein-Barr virus may cause chronic proptosis and a bilateral lacrimal mass effect. We provide a case of bilateral Epstein-Barr virus associated dacryoadenitis initially resistant to corticosteroid treatment requiring biopsy and confirmation by polymerase chain reaction of lacrimal tissue. Herein, we discuss the presentation with associated magnetic resonance imaging and histopathologic images, diagnostic dilemma, and treatment of an atypical case.