What role does diagrammatic perception (aisthesis), diagrammatic manipulation (techné), or diagram construction(poesis) play in aesthetics? Did the aesthetic relation between human beings and machines recently change? Independently of the question if AI will or will never (Smith & Landgrebe 2022) rule the world, we want to ask: How is human creative behavior and issues of aesthetics simulated, co-generated, or mimicked with the help of diagram- technologies and theoretically staged in diagram strategies/dramaturgies in AI aesthetics? If AI is conceived as imitation engine of collective intelligence (“We are AI“H.Herndon), what role do aesthetics and diagram play when considering topics of AI aesthetics, and how could a Peircean account of the diagram elucidate questions about AI aesthetics? How do (collective) aesthetic strategies that work with AI and machine learning tools use diagrammatic typification and simplification, e.g., in generating or applying aesthetic styles? Do artistic strategies of aesthetic blurring, ambiguity, and abstraction via Ai-apps mean more or reduced diagrammaticity? Can diagrams elucidate Machine learning ́s hidden layers (“black boxes”)? Does Ai aesthetic reduce aesthetics complexity to makable design problems (Does Ai aesthetic reduce aesthetics complexity to makable design problems (e.g. design to overcome the uncanny valley, design for social interaction, design for empathy, design of mimetic doubles/automata/human-AI-systems)? Are aesthetic style and design hacking a form of diagramming?