Students attain cultural knowledge to navigate college admissions, yet few studies investigate when and how students activate this knowledge in a relatively transparent system. Drawing upon 26 Taiwanese student interviews, this study unveils how students strategically use available information to illuminate each step of the admission process. I compare how middle- and working-class students activate cultural knowledge in high-, average-, and low-scoring segments. I show that the notion of cultural knowledge varies according to institutional contexts. In Taiwan, it refers to basic knowledge of explicit, yet complex rules which are taken for granted by the privileged, rather than implicit knowledge of the opaque, behind-the-scenes aspects of the system. I find Taiwanese middle-class students with average test scores take advantage of the information transparency to dramatically modify their strategies to gain admissions from prestigious universities. Students in high- and low-scoring groups, however, utilize this knowledge at much lower levels.