A 79 year old hispanic male presented with a non-specific chief complaint of decreasing vision OS > OD and ocular pain. He had a systemic history of insulin dependent diabetes, hypertension, and ischemic heart disease. Because he was a poor historian, no previous ocular history was obtained. Examination revealed dense epithelial and stromal edema, superficial punctate keratitis, and stromal infiltration. Anterior chamber angles were open. Applanation tonometry measured an elevated pressure in the left eye at 36 mmHg. At this point, were were faced with the challenge of managing unilateral corneal inflammation and increased intraocular pressure of unknown etiology. Subsequent follow-up examinations uncovered an unusual case of recurrent ocular Herpes Simplex disease which developed into a multiple management dilemma of active epithelial ulceration along with inflammatory stromal keratitis, trabeculitis, and glaucoma. The careful medical management of the condition is discussed, with an emphasis on balancing the concomitant use of anti-viral and anti-inflammatory agents, in conjunction with anti-glaucoma therapies to control the potentially devastating long-term sequelae of the disease. The presentation of serial photography highlights the disease process and resolution.