This project investigates challenges students face in environmental and sustainability education (ESE) practices in the form of ‘open schooling’ (OS), i.e. connecting education to identifying, exploring, and tackling sustainability problems in the school or the local community (European Commission, 2022; Van Poeck et al., 2024) The latter become the starting point of learning, where knowledge from school subjects assist in understanding and solving the problem. In this study an OS practice is implemented using a method called LORET (local relevant teaching) (Östman et al., 2013). Researchers have observed how ESE practices such as open schooling disrupt regular schooling practices. The conditions that create these tensions are referred to as the rhetoric-reality gap in ESE literature, as the intended purpose of traditional schooling collides with the visionary purposes of EE (Stevenson, 2007). The gap highlights the disconnect between status-quo values that mainstream schooling operates within with a focus on task solving, assessment and production of school work, and the visionary goals of environmental education, which calls for open-ended problem solving and transform the status-quo. (Stevenson, 2007; Vare & Burch, 2024). The aim of the study is to investigate the challenges students face within OS practices in relation to their existing schooling habits . We draw on in-situ observations in an explorative case-study in a Swedish middle school. We use the transactional theory of learning by Östman et al. (2019), based on the pragmatist work of John Dewey (1916). In this theory learning is seen ‘transactionally’ as a consequence of an individual’s coordination processes with the environment. Learning is understood as being triggered by a problematic situation when our habitual ways of thinking and acting are disturbed by changes in our environment (Dewey, 1929). This change needs attention (cognitively and/or bodily) if we are to continue with the activity. We then engage in an “inquiry” which involves experimentations and making relations to existing knowledge, skills, values or creating new relations, leading to the creation of a new habit. The empirical questions that guide our study are: 1. What problematic situations occur when students engage in open schooling projects? 2. Which habits of students, used in everyday school work, are disturbed in relation to the problematic situations identified? 3. How do students overcome these disturbances of habits and transform existing habits?