Purpose: To describe a case of massive retinal pigment epithelium (RPE) tear following a hypertensive crisis superimposed on chronic central serous chorioretinopathy (CSCR). Methods: A case report with a focused literature review was performed. Results: A 55-year-old man with a history of chronic CSCR presented with acute vision loss in the setting of a hypertensive emergency (blood pressure, 215/130 mm Hg). Multimodal imaging and clinical examination revealed a massive RPE tear in the right eye extending from the temporal periphery through the macula. The left eye demonstrated smaller RPE tears associated with macular scarring and intraretinal fluid. The right eye was managed conservatively and showed progression of the RPE tear over 1 month. The left eye was treated with an intravitreal faricimab injection, resulting in improvement of the intraretinal fluid. Conclusions: This case supports a potential 2-hit mechanism in which chronic CSCR-related RPE vulnerability, combined with acute hypertensive choroidopathy, leads to extensive and progressive RPE tearing. Patients with chronic pachychoroid spectrum disease and systemic hypertension may be at increased risk for severe RPE complications.