Objectives: In contemporary times writing is more important than ever, and spelling is a key transcription skill for efficient writing. While little is understood about the particular challenges some children experience when learning to spell, explicit instruction is known to improve spelling performance. The case study reported in this article forms part of a larger Australian mixed-methods study examining spelling acquisition, as represented by a stratified random sample of Australian students aged 8 to 12 years (n=1,198). The present case study utilizes spelling error analysis of dictated words, and narrative and expository writing, as well as semi-structured interview data from a randomly selected sub-sample of low-achieving spellers (n=8) and their teachers (n=8). Descriptive analyses of phonological, orthographic and morphological spelling errors revealed students’ common and unique challenges in learning to spell. Qualitative analysis of semi-structured interview data identified that the case study students lacked confidence in spelling and general writing, used ‘sounding out’ as their dominant strategy for spelling less familiar words, and displayed limited understanding or use of metalanguage associated with spelling and writing. Interview data from the respective classroom teachers revealed a lack of confidence in their ability to teach spelling, along with limitations in pedagogical content knowledge and instructional approaches. The findings highlight the need for improved understandings of ways to support students who find learning to spell challenging.