This chapter presents the qualitative design research study of the dissertation and analyses of students’ learning processes in Design Experiment Cycles 1 and 2. The analyses follow a content-related design research specification approach building on scaffolding analysis and use the ICAP framework and its content-specific substantiation for the basic analysis. The comparison of students’ algebra-specific processes in Cycle 1 and Cycle 2 reveals that only targeted scaffolds successfully focus students on the most relevant concept elements and algebra-specific processes. Cycle 1 analyses refine the algebra-specific learning trajectory by highlighting the importance of comparing meanings of variables for grasping letter variables. Cycle 2 data indicate that most observed processes align with intended scaffolding effects, while also indicating avenues for further improvement in the Cycle 3 design.