Residential care facilities (RCFs) provide 24/7 care to older adults with cognitive and/or physical disabilities and aim to provide person-centered care (PCC). Maintaining residents’ autonomy is important to provide PCC, for example, with shared decision-making (SDM). Residents are largely dependent on multiple stakeholders, which could jeopardize their autonomy, especially regarding unhealthy behaviors, such as smoking tobacco or drinking alcohol. This case study explores the dynamics of multiple stakeholders around four RCF residents regarding their alcohol and/or tobacco use. Four RCF residents who smoke tobacco and/or drink alcohol were selected from a previous study, and their (in)formal caregivers were additionally invited to participate. A qualitative research design was chosen, and semi-structured interviews were conducted. The Ethics Review Board from the Tilburg University School of Social and Behavioral Sciences (Reference: RP39) and the executive boards of the two participating organizations granted approval. Narrative portraiture resulted in four case descriptions. Two cases focused mostly on tobacco use, and two cases focused mostly on alcohol use. Multiple stakeholders were involved on different levels: family bought alcohol or cigarettes, and team managers supported care professionals. However, little interaction was found between stakeholders. In these cases, limited interaction between the stakeholders, including the resident, jeopardizes SDM and, in this way, PCC regarding residents’ alcohol and/or tobacco use. SDM on this topic could enhance interaction between all stakeholders involved, which could increase PCC. Finally, the cases indicate a constant struggle between protecting residents from adverse outcomes of alcohol and tobacco use and enhancing their autonomy.