A roofer's utility box includes non-rectangular sides angled downward from one end of the box to the other, defining a substantially trapezoidal box. Retractable leveling legs disposed on its downhill face extend below the box bottom to enable leveling its top surface. Roof anchors and a ridge tether on the uphill end, and a safety brace on the downhill end, secure the box in place. Lifting and towing handles cooperate with retractable castors to facilitate positioning the box. Masts extending upward from the box's downhill end, and a yard arm spanning between them, support a walkway plank to create temporary scaffolding supported by the box. A variety of exterior utility devices attach to the box and scaffolding masts, including trays, cutting and clamping surfaces and electrical and pneumatic outlets for use with power tools. The box interior may be fitted with an ice chest and/or sliding trays for convenient storage.