The interplay between student and teacher expectations about the requirements for successful learning in higher education (HE) can impact on successful student outcomes. This study aims to identify and understand the expectations that first year university students have towards essay production during their acculturation to HE. By examining the expectations their teachers have towards essay production, the extent of the alignment between the teacher and student expectations can be investigated. Furthermore, this study tentatively explores the impact that diverse educational backgrounds have on the formation of expectations for essay production between students and teachers in UK HE. This study identifies that although there are some areas of alignment between expectations of students and teachers, there are important differences related to plagiarism, interpreting essay questions, understanding marking criteria, and the availability of writing support. The greatest differences appear not so much related to different educational backgrounds, but instead with time spent in higher education.