Combined rhegmatogenous retinal detachment (RRD) and serous choroidal detachment (CD) present a significant challenge. No global standard of care exists for treating these complex RRDs. There is a lower failure rate when such detachments are treated with pars plana vitrectomy than with scleral buckle alone. The use of pre-operative steroids may not work in cases with moderate-to-severe CDs with severe hypotony where suprachoroidal fluid drainage is required to reduce inflammatory mediators, thus preventing proliferative vitreoretinopathy (PVR). We report a case of a 62-year-old male who had a combined RRD and severe CD with vitreous hemorrhage in the left eye (LE). There was extreme hypotony leading to a severely deformed and distorted globe with poor visualization of the fundus. The patient was started on 60 mg of oral prednisolone, and a posterior subtenon injection of 20 mg of triamcinolone acetonide was given to reduce inflammation and CD. However, despite one week of pre-operative steroids, there was severe hypotony. The patient was taken for pars plana vitrectomy with drainage of suprachoroidal fluid. Intra-operatively even after drainage of suprachoroidal fluid via inferotemporal posterior sclerotomy, hypotony persisted, and media was very hazy, precluding us from proceeding with vitrectomy in the first sitting. Oral steroids were continued, and vitrectomy was done in the second sitting, 72 hours later, with long-term silicone oil tamponade. Post-operatively patient had a well-formed globe with an attached retina and a good visual acuity. Our case thereby highlights that combined retinal and CD is a complicated diagnosis that presents with many pre-operative, intra-operative, and post-operative challenges. We could achieve good anatomical and functional success using a modified two-stage approach in our unusual case of combined RRD wth CD with extreme hypotony.