It is widely accepted that individuals with criminal convictions experience multiple disadvantage and deprivation, and, as a result, are considered least likely to progress to higher education (Unlock, 2018). The risk-adverse nature of higher education application processes further compound such disadvantage, even though there is no evidence to suggest that screening for criminal convictions increase campus safety (Centre for Community Alternatives, 2010). Drawing upon ethnographic data, the discussion critically reflects upon the development of one situated Learning Together initiative based within a University in the north-west of England. In doing so, the discussion highlights a series of emerging opportunities and competing contradictions that span over three key developmental areas: creation, progress and maintenance. We anticipate that the findings will go some way in opening up a wider debate about the sustainability of initiatives that seek to create dynamic educational partnerships between the higher education sector and criminal justice system more broadly.