Does authentic assessment or the perception of it affect how students study and learn? Does practical experience affect how assessment authenticity is perceived? And does practical experience influence how an authentic assessment affects student learning? Mixed methods design yielded insight into the answers to these questions. This article presents the results of a study on the relationships between authenticity perceptions of different cohorts of students, who differed in the amount of practical experience, their study approach and their perceived degree of professional skill development. The results showed some salient differences in how freshman- and senior-student groups perceive the same authentic assessment and how this assessment influences their learning. These results suggest possible guidelines for developing and using authentic assessments during a curriculum in which learning and working are intertwined.