Literature studies have shown that older persons face an array of challenges, among them parenting a delinquent grandchild. This study adopted both a qualitative approach and paradigm, supported by an explorative and a descriptive case study design. The study sampled eleven participants, and data were collected using in-depth interviews and focus group discussions with grandparents, a community committee member, and probation officers. Measures employed by grandparent households in tandem with the Department of Social Development were unearthed. These included, but were not limited to, corporal punishment, seeking assistance from relatives, seeking assistance from social workers, and creating attachment. This article recommends that the government prioritize the grandparents’ vulnerability to the dangers of parenting difficult children, either by freeing them from such a harmful environment, or putting measures in place to manage children in conflict with the law, with special attention to grandparent-headed households.