Transitions into an assisted living home (ALH) are difficult and may impact the well-being of older adults. A thematic analysis guided by grounded theory was employed to better understand how a transition into an ALH influenced older adults’ overall well-being. Individual, face-to-face interviews were conducted with a convenience sample of 14 participants at an ALH in the rural, southeastern U.S. Two central findings that influenced well-being during the transition process were revealed: loss of independence (sub-themes include loss of physical and mental health and loss of driving) and downsizing in space and possessions. The themes support and broaden the Hierarchical Leisure Constraints Theory, a Modified Constraints to Wellbeing model is proposed, and implications for older adult health care practitioners in ALHs are recommended. Further research is needed on the Modified Constraints to Wellbeing model and how to better describe these constraints to older adults’ well-being when relocating into ALHs.