This article presents a meta-interpretative synthesis of contrasting research studies about methodological and theoretical challenges for Swedish preschool teachers in systematic quality development work. The first challenge involves an awareness of producing documentation from different levels of preschool work. The second challenge concerns critical reflection of multi-documentation. The third challenge focuses on an awareness of theoretical approaches which can allow a deeper understanding of quality within preschool work. This article proposes that, even if there are tensions and epistemologically different interests in many of the methods of evaluation used in preschools today, there is a need for comprehensive methods and recurring reflections that places preschools’ pedagogical work in an ongoing process of developing quality.