Self-directed learning (SDL) has become a central pedagogical expectation in secondary and post-secondary education, particularly within boarding school contexts that emphasise independence, self-management and autonomous learning routines. However, students with elevated autistic traits often encounter persistent challenges in engaging with self-directed learning environments, despite demonstrating adequate cognitive ability and academic potential. In boarding schools, difficulties in independent learning are frequently interpreted as low motivation, poor discipline or lack of effort, resulting in interventions that prioritise compliance and behavioural monitoring rather than the underlying regulatory processes shaping learning preferences. This paper is conceptual and does not report primary data. Drawing on contemporary literature related to autistic traits, psychological regulation and learning autonomy, this conceptual review synthesises evidence to examine how autistic traits influence students’ preferences for self-directed learning through the mediating role of psychological regulation. Evidence across five interrelated strands which (a) autistic traits in non-clinical student populations, (b) psychological regulation demands in boarding school environments, (c) self-directed learning characteristics and expectations, (d) institutional and contextual influences in residential schooling and (e) psychological regulation as a mediating mechanism suggests that difficulties with emotional, cognitive and behavioural regulation significantly constrain students’ readiness to engage in self-directed learning. Across studies, psychological dysregulation manifested through heightened stress, anxiety, cognitive overload and reduced self-management capacity emerges as a key mechanism shaping students’ learning preferences. Rather than reflecting an aversion to autonomy, lower preference for self-directed learning among students with autistic traits may represent adaptive responses to regulatory demands that exceed individual coping thresholds. Building on this synthesis, the paper proposes an integrated conceptual framework positioning psychological regulation as a central pathway linking autistic traits to self-directed learning preferences in boarding school contexts. This reframing highlights the need for learning environments that align autonomy expectations with students’ regulatory capacities to support sustainable, inclusive and self-directed learning outcomes.