Giant strides in information technology at the turn of the century may have unleashed unreachable goals. With the invention of groupware, people expect to communicate easily with each other and accomplish difficult work even though they are remotely located or rarely overlap in time. Major corporations launch global teams, expecting that technology will make “virtual collocation” possible. Federal research money encourages global science through the establishment of “collaboratories.” We review over 10 years of field and laboratory investigations of collocated and non-collocated synchronous group collaborations. In particular, we compare collocated work with remote work as it’s possible today, and comment on the promise of remote work tomorrow. We focus on the socio-technical conditions required for effective distance work, and bring together the results with four key concepts: Common ground, coupling of work, collaboration readiness, and collaboration technology readiness. Groups with high common ground, loosely coupled work, with readiness both for collaboration and collaboration technology have a chance at succeeding with remote work. Deviations from each of these create strain on the relationships among teammates and require both changes in the work or processes of collaboration to succeed. Often they do not succeed because distance still matters.