We explored whether exposure to different kinds of comprehension tests during elementary years influenced metacomprehension accuracy among 7th and 8th graders. This research was conducted in a kindergarten through 8th grade charter school with an expeditionary learning curriculum. In literacy instruction, teachers emphasize reading for meaning and inference building, and they regularly assess deep comprehension with summarization, discussion, dialogic reasoning, and prediction activities throughout the elementary years. The school recently expanded, doubling enrollments in 7th and 8th grades. Thus, approximately half of the students had long-term exposure to the curriculum and the other half did not. In Study 1, metacomprehension accuracy measured with the standard relative accuracy paradigm was significantly better for long-time students than for newcomers. In Study 2, all students engaged in delayed-keyword generation before judging their comprehension of texts. Metacomprehension accuracy was again significantly better for long-time students than for newcomers. Further, the superior monitoring accuracy led to more effective regulation of study, as seen in better decisions about which texts to restudy, which led, in turn, to better comprehension. The results suggest the importance of early exposure to comprehension tests for developing skills in comprehension monitoring and self-regulated learning.