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New developments in Artificial Intelligence (AI) and digital ubiquity bring revelations of emerging smart cities. However, urban designers are particularly reluctant to become digital and use software that automatically generates cities. Instead, they return to traditional design skills such as creating scale models, sketching, notations and drafting. There is an increasing advocacy for design to a human scale, placemaking and liveable cities. This viewpoint asks questions about the application of AI and generative algorithms in digitizing urban design practices. It reflects on the possibilities of conjoining urban morphology and design theory into City Information Modelling (CIM) as a new digital tool for urban designers and reveals challenges in the ongoing development of new CIM software. Urban designers work within intricate design worlds with toolboxes that consist of customized design elements and symbologies. The design worlds consist of elements, rules and patterns and they act as holding environments for their unique diagrammatic design knowledge. CIM and AI should understand design worlds with customized toolboxes and provide help to automate repetitive behaviour patterns while designing.

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