Creole-speaking contexts are significantly underrepresented in language and literacy research yet present a unique context for understanding the nature of language and literacy development among numerous learners in the Global South. In the Caribbean in particular, the poor writing outcomes of Creole speakers across all levels of education has been a subject of lament for educators and policymakers for several years. Given the significant differences between the home and school languages, particularly in the areas of grammar and phonology, as well as the importance of these skills in writing, it is worth exploring the nature of writing challenges among Creole dominant learners in the Caribbean. This paper outlines an empirical study exploring the nature of writing challenges experienced by Creole dominant primary school learners in the Jamaican context. As part of a larger mixed-methods study, students completed a narrative writing task which was assessed with reference to an analytic rubric. Findings showed that beyond grammar, which has largely been the focus of extant literature, Creole dominant learners experienced significant challenges in lower-order transcription skills and higher-order oral language skills at the word, sentence, and text levels. Findings are discussed in line with the not-so-simple view of writing and recommendations for supporting the literacy development of Creole-speaking learners in the Caribbean are outlined.