Although writing is fundamental for effective language production, it is a difficult skill for second language learners, and this is evident in the numerous writing challenges students encounter. This mixed-methods study was designed to investigate the academic writing challenges Jamaican undergraduate students face and the perceived factors that hinder the development of their writing skills. Quantitative data were gathered and analyzed using the Daly-Miller Writing Apprehension Test, student and faculty perception surveys, and writing assessment scores, while qualitative data were collected from semi-structured interviews conducted with students and lecturers. Writing samples were collected from 100 students to identify the major challenges they had with academic writing. The findings reveal that the major difficulties students encounter are related to referencing, grammar, mechanics, lexical, and discourse challenges. Students and lecturers are of the perception that these challenges are influenced by a number of factors including students’ fear of writing, the Jamaican language situation, low motivation, and the lack of a writing across the curriculum initiative.