The status of offender rehabilitation has been influenced by the prevailing social climate, the promotion of ways to improve rehabilitation’s efficacy, and the well documented cycling of correctional imperatives. A renewed interest in offender transitions and reintegration has been apparent in recent years and most western correctional systems now feature policies and/or programs that address issues relating to the housing, employment, education and the broader ‘resettlement’ of offenders. However, this movement of correctional imperatives into the ‘social’ realm brings considerable challenges. Perhaps most significantly, the achievement of reintegration is dependent on juridical and community support in ways that other sentencing goals are not. Given the array of understandings of what ‘reintegration’ actually is, the abundance of programs claiming such a focus, and the reliance that reintegrative ideas have on community support, measuring the extent and nature of such support is seen as a useful exercise. With the above in mind, the goal of this paper is to identify legislative and community obstacles to the success of reintegrative ideals and policies. The paper first examines relevant legislation for references to reintegrative notions, finding a legislative ambivalence about such ideas. It then presents findings from a Victoria-wide survey of community views about the reintegration of ex-offenders. Participants in the community survey (n = 2635) were asked for their views about sentencing objectives, and the nature of their support for employment and housing initiatives. The results showed low levels of overall support for reintegration, with numerous more subtle distinctions being evident. The data also identify numerous areas where reintegrative programs are likely to be more readily accepted. The findings also indicate a need for targeted research into the correlates of community readiness for specific aspects of offender reintegration, and underlines the need for community education about the social implications of effective reintegration policies for urban, regional and rural communities.