The aim of this research is to analyze teachers’ and paraprofessionals’ work and reflections on assessments for learning in a Swedish compulsory special school. Research has shown that assessment for learning is a powerful tool to improve student achievement. The theoretical perspectives discuss concepts such as situated learning and collaboration. The research adopted a participatory design; the researchers followed four teams, totally 20 teachers and paraprofessionals’ work through video observation, discussions, feedback and lectures on assessment. The teams documented classroom teaching and assessment of students' abilities in different subject. The data in this study are based on teams’ written texts. The texts are analyzed using a qualitative content analysis and contribute to research on formative assessment by including teachers as well as paraprofessionals. Results show, that professions have developed their educational philosophy and their ability to give children feedback, which will help their learning. The results also highlight the discussion between learning and caring, regarding the duties of teachers and paraprofessionals. A challenge for the teams is to unite the children’s care needs with the curriculum knowledge requirements and ensure them to learn within a holistic perspective. Teaching and assessing students with extensive learning difficulties and in need of alternative communication is another challenge for the teams as well as awareness that change processes take time.