Amid Australia’s real estate boom, social housing sites are increasingly seen as prime areas for future urban development. In response, the NSW Government has announced the major redevelopment of large social housing estates, starting with the site of Ivanhoe in Sydney’s north-west, as well as selling off other social housing assets near the city centre to help raise capital. Consequently, social housing tenants are increasingly facing the prospect of being relocated. To facilitate this process, in 2014 the NSW Government introduced ‘My Property Choice’ (MPC), a choice-based letting system that allows social housing tenants to become more active in their relocation. MPC involves tenants using an on-site office to enquire about and bid for, via a ballot system, available social housing properties. As a relocation incentive, the offered properties are often more up-market and in better condition than average social housing properties; however, this comes with the caveat that these new properties are often distant from tenants’ original locations, affecting their existing social networks and proximity to some urban amenities. Drawing upon interview data collected from NSW Family and Community Services relocation coordinators (n=14) and social housing tenants (n=26), this paper examines the implementation of MPC as part of the current Sydney relocation processes, revealing tensions surrounding efforts to increase residents’ choice. Despite policy rhetoric emphasising resident ‘choice’, MPC emerges as a chance-based process as tenants seek to ‘win’ their desired relocation destinations. This process results in anxieties associated with limited understanding of the process and the ongoing concerns of ‘losers’ trying to secure appropriate properties.