Digital technologies have increased not only in society but also within early childhood settings. The provision of devices differ between settings and ranges from limited to well embedded, with centres deciding how much time children can spend on various technologies. Research around the types of technologies educators provide for children’s use is also increasing. What is missing from the current literature is how children engage with devices in play-based settings. I aimed to address this gap in the literature, by exploring how children engage with both working and imaginative technologies in their play and the educator’s provision of the various devices. The study was conducted in two kindergartens in Melbourne, Australia. I remained at each centre for 12 weeks, observing and video recording children’s imaginative play with technologies, and interacting with the educators to understand their provision of the devices. Using the Imaginative Affordance Framework, that I developed during my Doctorate, I analysed the data collected and determined findings. I presented the findings as six paradoxes that explained what was occurring in the research centres. These were: working technologies versus non-working technologies; solitary individuals working with devices versus groups of children on devices; play-based, child centred programmes versus adult controlled programmes; nature discourse versus technologies as not natural; traditional kindergarten activities versus newer technological activities; and, children learning to navigate the rules pertaining to working technologies versus their desire to play according to their own volition. I concluded my thesis with suggested professional learning opportunities, future research and implications for policymakers.