The results of deinstitutionalization are well known, but less information is available on the process of deinstitutionalization itself. This study sought to understand the process of deinstitutionalization in Ontario by examining the timing of individuals’ transitions to the community and the characteristics of individuals who experienced a change in the timing of their move. Data used were based on census information collected between 2005 and 2008 using the interRAI Intellectual Disability assessment instrument on all persons residing in Ontario’s specialized institutions. Analyses of characteristics at baseline by the anticipated transition year revealed the existence of significant differences between the groups. Comparisons of anticipated and actual transition years revealed that about 40% of individuals experienced a change in their transition year. Age, bladder incontinence, and number of medical diagnoses were associated with increased likelihood of moving earlier than anticipated, whereas family contact, presence of a strong and supportive relationship with family, psychiatric diagnoses, destructive behavior, and aggression were associated with higher likelihood of moving later. Careful attention to characteristics and level of need was paid at the onset of the deinstitutionalization planning process; however, the timing of transitions to the community was not “set in stone.” In the future, studies should not only examine the individual’s outcomes and quality of life in the community, but also should seek to qualitatively describe the individual’s and family’s experiences of the transition process. This type of information is invaluable for other jurisdictions in which deinstitutionalization is planned or under way.