Directed self-placement (DSP) allows for student agency in writing placement. DSP has been implemented in many composition programs, although it has not been used as widely for L2 writers in higher education. This study investigates the relationship between student placement decisions and students’ prior educational backgrounds, particularly in relationship to whether they had attended an English-medium high school or an intensive English program (IEP). Actual placement results via an exam were compared to 804 students’ self-placement decisions and correlated with their prior educational backgrounds. Findings indicated that most students’ DSP decisions matched actual exam placement results. However, there was a large number of DSP decisions that were higher or lower than exam placement results. Additionally, the longer students studied at an English-medium instruction high school, the more likely they were to place themselves higher than their exam placement. We conclude that DSP can be used in L2 writing programs, but with careful attention to learners’ educational backgrounds, proficiency, and sense of identity.