The Model of Human Occupation (MOHO) is an evidenced-based model of practice that occupational therapists employ to discuss and reflect on the occupational needs of clients. Custodial grandparents are one cohort of potential clients who experience considerable difficulty in adapting to the occupational challenges of their grandchild-rearing role, particularly in relation to schooling. Hence, this study aims to broaden current understanding of the volition, habituation, and performance processes that custodial grandparents work through in their daily drive to meet their grandchildren's educational needs. Thematic analysis was conducted on 49 custodial grandparent interviews. Critical intervention points exist during the custodial care-giving role, at which juncture grandcarers experience feelings of stress overload and self-doubt. It is at these junctures that custodial grandparents would benefit from occupational therapy (OT), but such OT intervention is difficult to initiate among the hard-to-reach grandcarer age-cohort. To reach grandcarers and meet their occupational needs it is recommended that OTs conduct a family unit strengths, resources, and needs assessment for each student referred to them for age-inappropriate behavioral issues. In conducting a detailed family background assessment, grandcarers by extension can be reached and their occupational needs can be met.