Collaborative learning occurs when two or more learners work together towards a shared goal, drawing on each other’s knowledge and competencies. It enhances both the learning process and outcomes, while also fostering collaboration—an essential 21st-century skill for professional and everyday life. A range of technologies has been recognised for their potential to support teaching and learning across various educational contexts. These include desktop computers, interactive whiteboards, multitouch tabletops, and tangible user interfaces. Such technologies have been applied in subjects like languages, mathematics, and science, and across all levels of education, from early childhood to higher and adult learning. Despite the increasing presence of technology in classrooms, concerns have emerged about its potential to limit peer interaction and collaboration. This study draws on four case studies, conducted over the past ten years, to explore how different technology-enhanced learning environments afford students’ face-to-face collaboration in STEM (science, technology, engineering, and mathematics) classrooms—contexts traditionally characterised by individual and quiet work. Case 1 involved a web-based tool designed to support undergraduate students learning programming. Case 2 combined a web-based tool with unplugged activities to develop mathematical skills in 5th-grade students. Case 3 used a tablet app to introduce equation solving to 3rd-grade students. Case 4 employed a tangible user interface app to support 5th-grade students in learning algebraic equation solving. We compared the strengths and limitations of these technology-enhanced learning environments in fostering student collaboration. Our findings highlight that each environment offers distinct benefits and challenges, depending on the subject matter, age group, and classroom context. We reflect on how these technologies can be effectively integrated into classroom practice and discuss the broader implications for educational technology research, learning tool development, and pedagogical strategies that promote collaborative learning.