Entering higher education (HE) is a critical moment for many students and one in which their educational experiences may change dramatically, but are students academically prepared? From a structured and supported environment, they enter a more autonomous and independent setting and little is known about their preparedness for this transition. This article explores, through the voices of teachers in schools and colleges, two aspects of preparedness for HE, independent learning and academic confidence, in order to more closely examine the challenges faced by thousands of new students each year. The findings highlighted differences in both terminology and approach between the two educational layers and contribute new insights to support universities in enhancing practice through a deeper understanding of the prior experiences of their new students through the lens of their teachers. Overall, the article highlights some significant messages about the gap between these two levels of education that cannot simply be left to the student to navigate.