This chapter explores the impact of digital technology on public spaces and the challenges policymakers face in keeping up with technological ad-vancements. The development of connected places, such as Smart Cities, has been facilitated by digital technology breakthroughs since the 1950s, where real-time data is collected and analysed for decision-making. The chapter discusses a study that combined speculative design with a walking method and digital space to investigate the potential benefits, risks, and challenges of deploying connected technology in public spaces. The research method-ology involved physical and virtual walkshops presenting fictional and re-al IoT sensor deployments. The findings highlight the opportunities and challenges of digitally connected systems, as discussed by the participants. The chapter concludes with insights, limitations, and recommendations for further research, emphasising the importance of diverse stakeholder in-volvement in technology implementation in public spaces and the role of speculative design in policymaking. Overall, this chapter contributes to the discussion on the role of speculative design in policymaking and the need for diverse stakeholder involvement in technology implementation in pub-lic spaces.