Using qualitative methods, this study explored workplace disclosure decisions made by employees caring for children and younger adults with disabilities or special healthcare needs and compared these experiences with those of employees caring for older adults when seeking family support at work. Nineteen semi-structured interviews included participants caring for children and younger adults with disabilities and older adults who were predominantly female, white, college-educated, and middle-aged. Employees in the sample had developed communication competence from prior experiences that impacted their ability to negotiate workplace supports to achieve positive outcomes. Differences found between the groups relate to the experiences of stigmatization and the use of formal flexibility supports. Findings highlight the need for employers to understand employees’ experiences of work-life fit when they care for children and younger adults with disabilities as well as those caring for older adults. Implications for work–family theory, workplace inclusion policies, and practices are discussed.