This article presents Octopus, a gamification model for assistance in ubiquitous care of chronic diseases. Octopus was projected to be generic, namely, to support any kind of disesase. Moreover, the model uses context awareness and the history of contexts visited by users (trails). This article describes the model architecture and its prototype. The prototype was tested in a simulated u-health scenario to evaluate its functionality and its potential to real applications. The results were encouraging and show potential for implementing Octopus in real-life situations.