In the act of massive data and breathtaking advances of artificial intelligence, social infrastructure promotes automation, digital engagement, and active presence. Digital democracy propagates the participation of growing number of people to interact with institutions and services, ensuring that decisions made by digital tools reflect human values. The future environment and its vitality will depend on the ability to use intelligent applications and “systems thinking”. In this project, I have been focusing on automated processes as part of the Macaque and Archspike platforms. The goal is to assess the performance of automation in planning and its role towards objective, rational thinking. I will examine how systems and users react on each other, producing continuous and bidirectional flow of information. The project brings scientific and industry experiences, successes as well as challenges of incorporating feedback loops in human-machine models. .