This chapter conducts an empirical study on the Internet of Toys (IoToys) with preschool-aged children in Finland, focusing on the strategies that contemporary character toymakers use to persuade players to nurture, connect and take part in social play. Four English-speaking IoToys were chosen based on their supposed innovativeness, popularity and availability on Amazon.com at the time of the research (September–October 2017) and were playtested with preschoolers who were 5–6 years of age. The study focuses on the variety of play affordances of the hybrid toys, which are both educational and entertaining, and investigates how these features are employed in play. By studying potential play patterns related to these toys, this study highlights preschoolers’ own responses to the affordances of the chosen IoToys.