Transportation network connectivity has been linked to positive urban outcomes, including increased rates of active transportation, reduced reliance on automobiles and other social and economic benefits. While many stakeholders in greenfield development processes have emphasized the positive benefits of connectivity and connectivity has increased in many U.S. metros in the past two decades, many street networks remain fragmented and local connectivity remains far below that of historic patterns. This paper explores barriers to and influences on connectivity outcomes in new community construction in the Phoenix metropolitan area, employing mixed qualitative and quantitative methods. Interviews were conducted with members from various stakeholder groups in the subdivision development process. Case studies were developed with space syntax and network analysis measurements to illustrate the influence of variables and stakeholders on the planning process. Participants illustrated a complex political and economic reality surrounding the concept of connectivity, with site conditions and development market dynamics playing the clearest roles in shaping connectivity. The result is subdivisions are achieving moderate levels of connectivity and improving from historic patterns of dendricity but remain entrenched in planning paradigms built around self-contained sites and the policy and market limitations for robust connectivity beyond individual developments.