Globe perforation following peribulbar anesthetic injection is a rare but dreaded complication that often results in poor visual outcomes. This case report is on a female patient who sustained vitreous hemorrhage, retinal detachment, and macular breaks due to a peribulbar block administered in the setting of cataract extraction. The retina was repaired with pars plana vitrectomy, endolaser of the peripheral retinal break only, and an internal limiting membrane inverted flap for the macular breaks to avoid the endolaser on the macular area, achieving stable visual outcomes. The authors discussed various modes of local anesthesia for vitreoretinal surgery, risks for globe perforations, and how to approach retinal detachment secondary to needle perforations, which are complex cases at high risk for proliferative vitreoretinopathy. Early recognition and intervention in eyes with an inadvertent perforation can lead to a good outcome. Eyes with a longer axial length, superior, and multiple perforations are at higher risk of developing complications such as retinal detachment and vitreous hemorrhage. Complications such as retinal detachment, macular injury, and vascular occlusion are risk factors for poor prognosis.