Upadacitinib is a selective JAK-1 inhibitor initially approved for the treatment of rheumatoid arthritis and recently psoriatic arthritis (PsA). We present a patient with Atopic Dermatitis (AD), Psoriasis (PsO), PsA and Alopecia Areata (AA) refractory to multiple agents however, successfully treated with upadacitinib. Our patient initially presented with refractory PsO and PsA, leading to treatment with ixekizumab. However, subsequent development of pruritic, erythematous scaly lesions, along with AA, prompted a shift to dupilumab. When distressing PsA and suboptimal outcomes with previous treatments persisted, prior biologics were discontinued and upadacitinib was initiated. Over a three-month period, the patient achieved complete clearance of PsO, significant improvement in AA and resolution of her PsA and AD. This report highlights the therapeutic benefits of upadacitinib in treating inflammatory cutaneous conditions like AA and PsO and further suggests a need for clinical trials to explore its broad therapeutic spectrum.