In the space of a few years, the provision of architectural services that rely on the digital outsourcing of documentation responsibilities to other firms—often located offshore in areas of the world with lower labour costs—has come to the forefront of the restructuring debate of the architectural sector. Today, the discussion about digital outsourcing cannot be reduced to the simple exploitation of rent differentials between distinct socio-economic and professional worlds. It must also reflect and examine the objective extension of the transactional market of architectural practices, where firms can reorganize their production strategically across a vast territory to remain sustainable or competitive. Even though the distant collaborations that underlie this arrangement are drawing more public attention than in the past, it is still difficult for nonanecdotal evaluations to take place, since the parameters currently employed in the analysis of this phenomenon have not yet been sufficiently developed theoretically. As a result, it is arduous for industrial scholars, or for those firms that have not directly taken part in such ventures, to assess the perils and possibilities of this emerging mode of service delivery in a balanced way. Building on work carried out for a research programme sponsored by the Australian Research Council, this article establishes a set of criteria and protocols to gauge, more systematically, the potential and viability of distant alliances. By adopting such criteria, it becomes clear that the evaluation of digital collaborations cannot be done in the abstract or solely through the use of office spreadsheets. It requires a thorough consideration of the socio-technical characteristics of the firms involved, and an in-depth analysis of their cultural routines.