Expanded dengue syndrome (EDS) is a well-described entity in the literature (after 2009), with various new atypical presentations being identified each year. We report a case of 38-year-old man who presented to the emergency department with high-grade, intermittent fever for 7 days along with myalgia and headache. He had multiple painless palpable purpura over both lower limbs and breathlessness from the 4th day of fever. On admission, purpura progressed in the severity and dry impending gangrene of the toes of both feet developed. Blood cultures turned out to be sterile, and other infectious markers (malaria, scrub typhus, and chikungunya) were negative except for dengue serology (enzyme-linked immunosorbent assay-immunoglobulin M [ELISA-IgM]). Skin biopsy confirmed to be cutaneous small-vessel vasculitis. The respiratory distress was due to myocarditis (supported by raised NT-pro-BNP levels) and pulmonary edema. He also had possibly hemolytic anemia due to microangiopathy. Although there are many EDS cases of dengue myocarditis reported till date, dengue resulting in widespread endothelial activation and extensive vasculitis (small vessel due to purpura and medium vessel due to gangrene) is a rare phenomenon.