This paper presents insights from five case studies with 173 students aged 11–14 years old across three countries in Europe, exploring the integration of design thinking (DT) and emerging digital technologies in K-12 education. The study aimed to understand the impact of DT and digital technologies on the development of students’ 21st-century skills and capture the challenges students and teachers face. The focus is to give evidence-based recommendations for teaching using the DT approach. Despite the positive student reports on developing communication, collaboration and programming skills, other skills related to research and reflection, and understanding of DT were rather less developed. The main challenges teachers faced were related to time constraints, difficulties in using the technologies, lack of clear instructions, and limited understanding of the DT process. Seven practical recommendations on how to effectively teach and learn DT with digital technologies are presented. These are accompanied by the Exten. (D.T.)² Digital Design Thinking Model, an innovative framework designed to guide the use of DT with specific digital technologies across K-12 education.