The Internet of Things (IoT) has transformed numerous analogue products into IoT products with embedded sensors, advanced features and novel experiences. As these connected objects become ubiquitous, designers have shifted from a tool-oriented to an experience-oriented approach. However, the focus on maximising living efficiency and profit growth has often obscured the importance of pleasurability and experimentation in designing IoT products. Recognising the historical and psychological significance of pleasure in human experiences, this thesis proposes “pleasure-driven design” as an overarching concept for designing interactive product experiences that prioritise pleasure. While several general pleasure-driven design methods exist, they have not adequately addressed the distinctions between analogue and IoT products in terms of pleasurability, leaving a gap that this practice- based design research seeks to fill. Additionally, concerns over privacy and automated decision-making in IoT objects pose challenges to designing pleasurable experiences. Therefore, this work explores new possibilities for pleasure-driven design by leveraging the transformation of analogue products into IoT products. This work adopts an emergent methodology that integrates a research-through- design approach with a mixed methods approach, employing multiple methods including questionnaires, workshops, material speculation, co-speculation, technology probes and interviews. It begins with a literature review outlining the importance of pleasurable experiences in IoT transformations, analysing the role of pleasure in experience design and assessing existing pleasure-driven frameworks and IoT creativity-supporting tools. The exploratory practices identify differences between an IoT product and its analogue form in terms of pleasurable experiences and uncover deficiencies in current frameworks. Subsequently, the Internet of Things Transformations for Pleasurable Experiences (IoTT for PLEX) Framework is developed to support designers in delivering pleasurable experiences by utilising IoT transformations as materials and to enable design researchers to explore pleasure- driven design in this context. The framework is initially tested with designers and then with human-computer interaction (HCI) researchers through material speculation. Based on the new framework, the CloudPlanter – a technology probe and research product – is developed by the author and applied in a co-speculation experiment involving four pairs of participants to explore the future relationship between humans and networked objects. This thesis makes a valuable contribution to both the design and HCI research communities by expanding upon existing pleasure-driven experience design approaches specifically for IoT products and uncovering the mutual influence between pleasure-driven design and IoT transformations. The major contribution of this PhD project is the development of the novel IoTT for PLEX Framework, proposed as a new design and research method for exploring pleasure-driven design through IoT transformations. The research also generates knowledge at an intermediate level, including reflections on applying established approaches and an emergent methodology of investigating pleasure-driven design within the specific contexts and cases of IoT transformations. The thesis, presented as an annotated portfolio, embodies and enacts design theories. It offers new possibilities that should help designers create novel experiences through IoT transformations, inspire future research in IoT experience design and empower the IoT product industry to create more pleasurable and meaningful products.