Iris retraction syndrome (IRS) is an uncommon condition caused by retinal detachment that is characterized by back bowing of the peripheral iris, leading to a deep anterior chamber. It is commonly associated with ocular hypotony, ciliochoroidal detachment, and anterior proliferative vitreoretinopathy. We describe a case of a 66-year-old man presenting with 2 weeks of right eye pain, redness, and iris heterochromia. The patient was diagnosed with IRS secondary to a chronic retinal detachment. Initial management with topical steroids and mydriasis allowed resolution of the iris retraction and heterochromia, normalization of intraocular pressure, and improvement of choroidal detachment. Subsequent vitrectomy with endolaser and oil tamponade led to successful detachment repair. Initial pharmacologic management allows a more controlled approach to the repair of retinal detachment associated with IRS. The patient’s presentation is consistent with the hydrodynamic hypothesis of IRS.