How in-home disability support workers adapt what they learn in manual handling classroom training sessions to the circumstances of their work (i.e., their clients’ homes), is central to their own safety and that of their clients. In the in-home work setting there is no “expert” for newly trained workers to closely observe or on whom to model their work practice. A particular concern, therefore, is the degree of transfer or adaptability from classroom training sessions that may assist these workers to enact safe practices, as their musculoskeletal injuries continue to occur at unacceptably high rates. Consequently, understanding how best to support these workers initially learn their occupational practice may offer considerable procedural benefits across the entire arena of working well and safely. Contemporary accounts of learning emphasise the importance of immediate social partners such as teachers and co-workers. Yet, much of our learning for work occurs without such experts. So, we need better understandings of how individuals learn from different educational experiences and adapt what they learn to their practice, and also how this learning occurs in the absence of expert guidance. A case study approach, comprising two separate practical studies, was adopted for this inquiry, which aimed to explore the personal, situational and instructional bases for realising effective learning in the absence of expert guidance. Study A comprised an exploratory investigation in which a community service organisation’s existing manual handling training situation was appraised by way of semi-structured interviews and direct observation of support workers, and a trajectory for learning in situations of relative social isolation was proposed. Study B comprised an intervention, where the proposed trajectory was implemented for a group of new support workers learning manual handling. The effectiveness of this program was appraised, again through semi-structured interviews and direct observation. A reconciliation of both studies led to conclusions about the best ways that learning in relative social isolation may progress.