This chapter explores the struggles that high school and university students in Denmark experience and try to cope with, through the perspectives of study counselors. Scholars have lately described a relation between students’ felt pressures and an increase in diagnoses such as stress, anxiety, and depression as well as increases in the non-medical use of prescription pharmaceuticals for enhancement purposes. While counselors have a unique position in the educational system as someone who is there to support the students, they are also witnesses to the changes that student populations experience over time. The chapter is based on in-depth interviews with 36 counselors at different universities and high schools in Denmark and examines how counselors cope with new developments in the educational system as well as new kinds of student challenges and struggles that go beyond issues with performance and perfection.