In this chapter, we discuss the issue of implementing Realistic Mathematics Education (RME) in the English education system over a number of years and education sectors. We also consider the experience of one of us in the Cayman Islands, a British overseas territory with an education system that is influenced by British tradition, but is distant from many of its politically driven accountability pressures and measures. We illustrate first the challenges of developing an RME approach which is operable within the English system, highlighting the issues of student expectation, dominant didactic practices and assessment, all of which influenced what we were able to do. Second, we describe the outcomes of interventions in England at early secondary school level (age 12-14, Key Stage 3) and at General Certificate of Secondary Education (GCSE) level (normally age 15-16, Key Stage 4, but also available in post-16 education). Finally, Frank Eade describes his experience of building on our early work to develop an RME approach in the Cayman Islands. We conclude with a discussion of the lessons learned from these challenges. We argue that despite the problems we encountered there are reasons to remain optimistic about the potential of an RME approach in the English system.English mathematics education traditions have had a well-documented impact on classroom cultures and on student experiences and expectations, all of which present challenges for the implementation and impact of an RME approach. In particular, student performance in public examinations is used in systems of school measurement and accountability, often leading to 'transmissionist' classroom cultures that empha-