Success with academic writing is generally acknowledged as a crucial factor in university students’ academic success, and it has been an important focus of higher education research for many decades. Educators continue to face challenges teaching and supporting the academic literacy development needs of increasingly diverse student cohorts entering university, including those who enter via alternative pathways such as enabling education programs. Academic writing pedagogy is influenced by a variety of theoretical models; however, it has been noted that traditional ‘study skills’ and ‘academic socialisation’ models are dominant influences. These models have been challenged for perpetuating deficit views of students’ difficulties with academic writing, leading to pedagogy that aims to ‘fix’ the student rather than address the underlying causes of difficulties, particularly for non-traditional students. The emergence of an alternative ‘Academic Literacies’ theoretical model (Lea & Street,1998) has prompted alternative conceptualisations involving reframing academic literacy as plural (‘academic literacies’) and shifting to a view of multiple literacy practices situated within historical, political, social and cultural contexts (Street, 2015). While this model challenges traditional deficit framings of students’ difficulties with academic writing, some researchers and educators have noted there are practical challenges applying the model’s principles at structural and practice levels. Consequently, there have been calls for further investigation of academic writing in situated contexts to obtain a more nuanced understanding of the contextual factors that influence literacy events; to provide alternatives to deficit explanations of students’ difficulties with academic writing; and to stimulate the development of context-sensitive academic writing pedagogy that moves beyond a narrow focus on texts and students. This study aims to address these calls through a closer consideration of the contextual factors that influence an assignment event in a university enabling course. The study investigates assignment-related activity connected with a specific assignment event in a university enabling course using a holistic, activity-centric approach. The study uses Engestrom’s (1987) third generation Activity Theory, an activity systems analytic lens, and relational thinking that considers both the “human and more-than-human” aspects of academic writing (Burnett & Merchant, 2020, p. 46) to investigate the assignment event. The study is grounded in an interpretivist research paradigm and uses qualitative, exploratory, case study methodology. Data were collected from individual, semi-structured interviews with seven academics and twelve students, over two offerings of the course; other data collected included course artefacts and researcher notes. Data analysis was conducted using content analysis techniques, including conventional, directed and summative approaches. The data were analysed using NVivo 15 software and manual coding processes, using both deductive and inductive coding methods. The findings revealed how a range of context-specific factors related to Tools, Rules, Community and Division of Labour enabled or constrained academics’ and students’ efforts to achieve the Object(ive) of activity. In addition, a number of disturbances in the free flow of activity were identified which indicated a range of underlying systemic contradictions (Engestrom, 1987). The findings revealed the power of contextual factors to influence how an assignment event is perceived, taught, supported and experienced by participants. The study’s findings produced a more nuanced and systematic understanding of the nature of assignment writing in a university enabling course and highlighted how a focus on activity systems can offer an alternative to deficit framings of students’ difficulties with academic writing. The study provides educators with insights that can be used to guide flexible and context-sensitive academic writing pedagogy that enhances enabling students’ success with academic writing.