The digitialization of planning has taken place in a context where planning work is on-going and cannot be halted, and in which there are embedded institutional and technical systems and practices, as well as a number of technical, regulatory and socio-cultural data frictions. This context has led to a sub-optimizing approach to digitialization. In this paper, we examine the digital mediation of planning through an in-depth case study of a multi-scale planning development and control data ecosystem in Ireland. We detail the incrementalist nature of the digital turn in planning and how this institutionalizes a ‘good enough’ digitialized planning system; that is, a system that is functional and performs essential tasks, but not necessarily in an optimal manner and which is always open to potential improvements. We develop a conceptual basis for assessing ‘good enough’ and through its application contend that ‘good enough’ planning is a sufficient and reasonable state of affairs given the substantive challenges of creating and maintaining a complex data ecosystem and that there are incremental limits to achieving ‘better planning’. As such, any technological solutionist claims promising to radically reconfigure and fix planning’s operation shortcomings, such as the introduction of artificial intelligence tools, require careful assessment.