Conference proceedings often present successful research and best cases. This paper presents a case that initially did NOT develop as anticipated and reflections as to why outcomes were different than expected. It also suggests important factors to consider before similar activities are undertaken in the future. The case presented investigates reflective assessments for the module "Current Issues in Edutainment Software Design", given to seniors in the Edutainment Software Design program at Halmstad University, Sweden. Throughout their program, these students have been indoctrinated to engage in self-reflection. Module assessments included development of both individual and group papers. Moreover, all students should reflect on their own learning process and produce their thoughts in a diary. Analysis of texts indicate that self-reflection "on command" proved difficult for these students, although they had been "trained" to reflect. Compared with two other groups lacking a similar, reflective background, instructed reflection seemed easier for "untrained" students. © 2003 IEEE