We are witnessing rapid growth of inter and intra-organizational telework in many different forms: distributive project teams, telecommuting, mobile work, business to-employee, employee e-business, and virtual corporations. Despite the increasing prevalence of distributive work and its importance in creating business value, our understanding of its success factors is limited. Among many prospective factors, task characteristics, communication quality, and technology support have been mentioned frequently as key components for successfully running telework. Communications quality and technology support seem the direct result of operational design in managing the virtual process; while task characteristics of workers are typically pre-determined, unless they are modified for telework. This paper discusses the implications of chosen variables on telework success from a fit theory perspective. It focuses on examining the implications of two- and three-way alignments among task characteristics, communications quality, and technology support on in a distributive work setting.