A 41-year-old male with type 2 diabetes mellitus (T2DM) presented with complaints of recent onset limb weakness, diffuse body rash and fever. Computerized Tomography (CT) scan of the brain did not reveal a stroke but laboratory investigations of the patient portrayed multi-systemic involvement. Naso-pharyngeal swab for severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) was taken which resulted as positive. Soon after, a biopsy of the skin lesions revealed histo-pathological features of leukocytoclastic vasculitis. The patient was further investigated for connective tissue disease and vasculitis only to yield a negative result for all relevant antibodies, with the exception of the anti-phospholipid antibody which was positive. The patient suffered through a complex and prolonged hospital stay that required the input of multiple sub-speciality teams. Although initially presenting with a normal chest X-ray the patient went on to have severe bilateral pneumonia and a progression of initial skin rash leading to severe necrosis of the left foot with dry gangrene of the left big toe. Due to these issues, coronavirus-disease-2019 (COVID-19) aimed therapy was started along with multiple skin debridements, antibiotics and eventual amputation of the patient's affected large toe. The following case-study details all the before-mentioned events with discussion of the possible reasons behind the patient's presentation and eventual outcome.