Dewey famously believed that we learn through experience, through which we build up habits. Education should be about developing good habits. Experience for Dewey, is not an individual possession but grows out of social interaction, which always takes place in a given culture. Dewey's views on culture are significant in relation to a current issue in education in England, namely the legal requirement for teachers to report students who express ‘extreme views’, under the Prevent Strategy. The article first gives the current context in recent policy implementation in England and discusses how it raises ethical dilemmas which profoundly affect what it means to be a teacher. This is then illustrated through a vignette, a narrative of a newly qualified teacher living a dilemma raised by the policy. Consequences for the development of democratic education and education for democracy emerge from considering Dewey's views on experience and culture in relation to the teacher's dilemma. The conclusion suggests some ways forward in the face of the difficulties raised by the Prevent strategy reporting requirement.