In engineering education, as well as in the society at large, there is an increasing focus on sustainability and sustainable development. The CDIO Standards and the CDIO Syllabus has been substantially updated to meet and drive these changes. Progressive engineering programs have by now made substantial progress in integrating environmental aspects of sustainability and sustainable development into the curriculum. However, the integration of social aspects is generally considered to be more difficult and is therefore lagging behind. This explorative research paper provides insights in efforts to integrate elements of gender equality, diversity and equal conditions (GDE) in three courses on bachelor’s, master’s, and doctoral level. The focus is on the development and implementation of reflective assignments, where a theoretical framework is used for characterizing different levels of reflection. The work has been performed by use of an action research approach that has involved close dialogue and collaboration between researchers, pedagogic developers, teachers, students, and education leaders. The paper hereby contributes with multiple perspectives on GDE integration, and significant challenges are discussed. The paper also contributes with concrete examples of reflective assignments, learning activities, and literature that can be useful also in other contexts.