Older people who become homeless have attracted increasing attention in North America, Western Europe and Australia over the last 20 years, but there have been few projects dedicated to their support, and even fewer studies of the outcomes. This paper reports a longitudinal study of the resettlement of 64 older people who were rehoused into permanent accommodation from homeless people's hostels in England. Their progress was monitored for two years by face-to-face interviews. The theoretical model was that the outcomes of rehousing are a function of personal factors and behaviour, the support that people receive, and the characteristics of the new home. After 24 months, 28 respondents were housed and ‘settled’, 10 were housed but ‘unsettled’, 11 had abandoned their accommodation, and six had been evicted (nine had died or ceased contact). The factors that significantly associated with remaining housed and settled included: previous stable accommodation histories, revived contacts with relatives, taking up activities, and regular help from housing-support workers. Unsettledness and tenancy failure associated with prolonged prior homelessness, worries about living independently, and continuing contacts with homeless people. Rehousing older homeless people successfully is difficult, particularly among those with long histories of homelessness and instability, and more needs to be known about the types of accommodation and the types of support that promote tenancy sustainment.