The purpose of this study was to highlight a potential alternative to additional surgery for management of retinal redetachment through the use of additional facedown positioning with silicone oil tamponade. Retrospective case series of two patients evaluated with examination, multimodal imaging, including fundus photography, optical coherence tomography, and fluorescein angiography. In Case 1, a 70-year-old female patient underwent surgery for a full-thickness macular hole with associated macula-off retinal detachment, but experienced a recurrent detachment and underwent a second surgery with silicone oil placement. Another recurrent detachment was found. The case was managed conservatively with facedown positioning, resulting in resolution of subretinal fluid and improvement in vision. At follow-up, the retina remained attached with stable vision. In Case 2, a 25-year-old male patient underwent a surgical repair for proliferative vitreoretinopathy retinal detachment with a scleral buckle, cryotherapy, and external drainage. After multiple redetachment surgeries with retinectomy and oil placement, another tractional redetachment of the fovea was noted. Management was with facedown positioning, and follow-up evaluation showed resolution of the subretinal fluid and improvement in vision with stability for greater than 2 months. For recurrent retinal redetachments with silicone oil in place, an additional week of facedown positioning can result in anatomical success and be a viable alternative or bridge to invasive surgical interventions. This approach may have greatest utility for patients who are poor surgical candidates without new peripheral pathology.