The author reflects on how she has used technology as a language teacher since the mid-1980s. She describes the evolution of technology in language learning pre- and Internet tools, from "blended learning" to social media. She concludes with the telecollaboration projects she has been recently working on and the issues they have found when teaching language students. She summarizes the findings in the projects based on the reflections from colleagues and students that in telecollaboration it is desirable to: (1) carefully scaffold the introduction to online interaction and provide many lines of digital support; (2) discuss the multimodal multiliteracy demands of telecollaboration before, during and after the project with all participants involved; (3) raise awareness of "intercultural cyberpragmatic competence 2.0"; (4) have a dialogue with expert students to design cyberpragmatic guidelines on "rules of telecollaborative discourse engagement" and tailor-made "netiquette" exercises; (5) test the e-learning platforms with partners before the beginning of the project; (6) not make any assumptions about the level of digital literacy of the students or staff involved; and (7) avoid "essentializing" and "generalizing", and provide some socio-cultural, geographical and historical information on the partners' context. [For the complete book, "10 Years of the LLAS eLearning Symposium: Case Studies in Good Practice," see ED577046.]