Over the years, language teachers have tried to design diverse and innovative collaborative language learning activities around readily available technology in the hopes that it will make language learning more meaningful, fun, and efficient. Nevertheless, technology is known to facilitate and sometimes hinder various forms of collaboration among language learners in face-to-face, blended, and online learning contexts due to several technical and non-technical reasons. Moreover, language learners’ lack of knowledge and skills to work collaboratively with others often leads to “unsuccessful” collaboration. This presentation explores some of the opportunities and challenges of employing technology-enhanced collaboration and emphasizes the importance of introducing language learners to the basic principles of collaborative learning that are often taken for granted. Several examples of collaborative face-to-face and online language learning activities are used to illustrate the intricacies of collaborative language learning design and highlight some lessons learned from the language classrooms.