Space syntax has established itself as a significant field of research into architectural and urban phenomena through the analysis of spatial configuration. Analyses that predominantly consist of variations on modelling spatial configurations as systems of axial lines, segments, convex spaces or isovists with further refinements. This analysis builds on the process of, as stated in the Social Logic of Space, first making discrete units out of continuous space, so as to create a system that can be analyzed, and then subjecting this system to analysis. The procedures of creating these discrete systems have seen many iterations, lately often employing a range of processes to road center line maps or similar existing geographical information or, increasingly dominantly for buildings, VGA analysis where isovists are distributed evenly in a grid in the space subject to analysis. This has allowed for more rapid analysis of larger sets of data and ostensibly less impact of human decisions in constructing the analytic models. At the same time, theoretical developments have increasingly looked to cognition to explain statistical results and to theorize the spatial units employed in syntactical analysis. This work has been important for the field. However, some important questions still await robust theoretical reconciliation. For instance, isovists, argued for as representation of vision, are employed both to analyze visibility and accessibility while the scale and type of object or material boundary that is considered a boundary in an axial line or convex space map varies. This article does not strive to provide a final resolution to these challenges, but discusses and refines the theoretical basis to provide potential paths forward. In this discussion, the article compares spatial configuration as the understanding of the combination of construction of pre-defined entities to spatial configuration as the result of subdivision and articulation of spatial differentiation in several ways, which incorporates cognition as an active faculty that operates in relation to intent and background of whomever is concerned, but also allows to consider the potential of different cultures embedded in cognition through notions of salience and articulation. It suggests that some of the difficulties in finding a clear-cut definition of e.g. ‘convex space’ lies in that rather than a geometric property of ‘space’, one might look to their formation and articulation by material boundaries as culturally and situationally conditioned. This allows for a more dynamic yet not completely relativistic theoretical ground for developing analytic modelling further and meeting challenges that are yet theoretically unresolved.