We propose a novel model for learning environments to target the characteristics of digital natives and to improve informal learning practices, i.e. the exploration, discovery and self-monitoring of learning content and the reflection on learning activities. The Mobile Playful Learning Environment (MPLE) model is defined as consisting of seven main features (mobile user context, data collection and analysis, learner visualization, self-monitoring, persuasion, playfulness, and micro-learning) intended to encourage continuous usage and self-reflection. As a case study we developed TICKLE, an application that implements the MPLE model to re-activate and re-motivate youngsters at risk for school dropout, for learning by stimulating curiosity and engagement through the recognition of non-formal learning opportunities. [For the full proceedings, see ED622227.]