Theory suggests that teacher encouragement can aid students’ educational progress, but there are not yet quantitative inferential studies that assess its longer-term impact. With data from the Longitudinal Study of Young People in England (LSYPE), I use propensity-score matching to investigate whether encouragement influences the likelihood of students enrolling in (1) advanced high school (A-level) courses and (2) a university degree course. Model estimates suggest that encouragement does have a significant positive impact on both outcomes. In addition, I investigate whether encouragement effects vary according to parental education and the given student’s prior academic achievement; it appears that the impact is greatest for those students in the middle third of academic achievement as well as those with lower levels of parental education. These findings have important policy implications, especially as it seems that teacher encouragement has the greatest influence on those students most likely to be on the margin for university attendance.