Abstract. Learning a new language includes multiple aspects, from vocabulary acquisition to exercising words in sentences, and developing discourse building capabilities. In most learning scenarios, students learn individually and interact only during classes; therefore, it is difficult to enhance their communication and collaboration skills. The prototype game described in this paper aims to fill this gap and improve the students' learning skills in a smart learning environment suitable for a problem-solving game. In addition, the game is also an useful tool for teachers because of the integrated chat analysis that enables the identification of the most predominant points of view and the overall level of collaboration between participants. The game is developed as a bot on the Slack chat platform and reacts to user commands. At the end of a game round, the bot is to save the conversation transcript and send it to the ReaderBench framework for further chat analysis. Keywords:Collaborative serious games · Smart learning environment Conversation analysis · Online chat · Language learning ReaderBench framework MotivationOne important task in a 'smart' learning ecosystem is to help language learning both native children and foreigners that enter in that ecosystem. However, language learning is a long-term process that includes vocabulary acquisition, accompanied by its usage in a coherent manner, within more and more elaborated contexts. The language learning process that is currently available in schools and universities is based on memorizing concepts, repeating them and using them in sentences [1]. Our study focuses on enhancing these methods by incorporating them in a smart learning environment that makes use of gamification. Starting from serious games centered on vocabulary acquisition, such as Semantic Boggle [2] and Semantic Taboo [3], our aim is to move forward towards evaluating how students understand written texts [4].In this paper we introduce a prototype serious game that focuses on improving the collaboration and communication levels of students. The game, The Robbers and the Others, is a problem-solving role-playing smart chat environment in which students are