Many transport organizations seek to develop seamlessly integrated computing environments. A central problem in attempts to realize such ubiquitous transport systems is the divide that exists between stationary transport management systems and mobile applications such as embedded vehicle sensor networks and in-vehicle services for message handling. Originating from different Innovation regimes, these technologies are heterogeneous in that they rely on different technological platforms and knowledge bases, as well as the institutionalized settings from which they have emerged. This paper assesses how the mobile-stationary divide plays out in practical efforts to develop ubiquitous transport systems in road haulage firms. This assessment is conducted through a multiple-case study that identifies socio-technical challenges associated with this divide. Building on this assessment, the paper contributes a set of implications for enterprise-wide ubiquitous computing environments where coordination of diverse sets of mobile units is central to organizational performance. On a general level, these implications are important for any organization attempting to integrate mobile and stationary information systems.