The purpose of this study is to investigate how assessment processes in secondary school Physical Education and Health (PEH) are manifested in PEH teachers’ concrete grading based on the new Swedish curriculum from 2011. Three major questions are formulated: Which difficulties and possibilities do PEH teachers experience during assessment based on the new curriculum? How do they motivate their grades? Which dilemmas do they describe in connection with their grading? The curriculum theories by Bernstein and Swedish theorist Linde were chosen as theoretical framework. Furthermore, a hermeneutic perspective was applied in order to interpret and analyse the results from video recorded interviews. The results show that the new curriculum and syllabus are described as more structured and more interconnected than the previous ones. The new grading scale, the explicit syllabus and the fact that teachers have to offer a wider spectrum of activities are described as strengths. Grades are meticulously documented since this is a way to justify the grades both for the pupils and their parents. Almost all participating teachers in the study use matrices to document their assessments. Theoretical knowledge has gradually become more important in PEH, for example Health is mainly assessed based on theoretical assignments. However, the constant assessment has become so comprehensive that the PEH teachers fear that the joy of being active will decline. The difficulties experienced in relation to the new curriculum are, to a large extent, focused on the new grading scale and the description of what is required to obtain a certain grade. Teachers are hesitant as to the meaning of expressions like “to a certain degree”, “relatively well” and “well”. They feel insecure in their assessment, for example how to handle the proportions between different capabilities. It is obvious that further in-service training is necessary in order to obtain more equivalent grades. The requirements for each step of the grading scale must be clarified.