This paper describes three case studies, where language learners were invited to use “LingoBee” as a means of supporting their language learning. LingoBee is a mobile app that provides user-generated language content in a cloud-based shared repository. Assuming that today's students are mobile savvy and “Digital Natives” able to engage in language learning autonomously using technology, initial studies were conducted with little or no intervention by the language teachers. However, the support and guidance provided within a teacher-led context can impact positively on learner engagement and use of LingoBee. The authors discuss this hypothesis using three case studies conducted in three European countries, within the EU LLP project SIMOLA, Situated Mobile Language Learning. This paper answers the research question: Does the level of the support and guidance, pedagogical approach and prior learning impact on learners' engagement and use of LingoBee? An earlier version of this paper was presented at the IADIS Mobile Learning 2013 conference.