In 2018,an estimated 27 percent (13 million) of Kenya’s population lived in cities and towns, of varied sizes, across the country. Towards the year 2050, this share will approach 50 percent of the total country population, which will be an equivalent of 44 million people. Kenya is thus undergoing an urban transition, which will induce structural transformations in social, economic and spatial development aspects. To effectively and efficiently manage this transition, the country must develop the requisite urban planning and management capacities, both at the national and county levels. At the county level, there are various interventions required to attain a fit-for-purpose planning system, which is responsive to local needs and aligns such needs to the national vision for a desirable urban future. However, to formulate the appropriate interventions required [to achieve the desired planning system], it is important to understand the issues confronting the current planning system, as a critical point of departure.