This paper explores the letter-writing component on the English portion of Myanmar’s University Entrance Examination, also referred to as the Matriculation Examination. Very little has been published to date regarding this examination in general, and this paper appears to be the first to address the letter-writing portion of this exam in detail. 165 letter-writing prompts used on the actual exams from 2009 to 2013, as well as six marking schemes used from that same period to assess examinee responses were analyzed. Inconsistencies in the difficulty level of the prompts as well as potential issues with the reliability of the current marking scheme(s) are discussed. The researchers ultimately advocate that the Ministry of Education and Myanmar’s Board of Education revise their current approaches to creating letter-writing prompts and consider developing a more contextually-specific and dynamic assessment instrument capable of serving in a formative capacity in classroom-based instruction while also serving the assessment needs of examiners.