Returning to the community after being incarcerated brings many challenges. In Victoria, Australia, a government-funded contract with non-government organisations (NGOs) allocates reintegration workers to assist with the post-release social integration process. In 2020, we interviewed reintegration workers to explore how they performed their roles before and during the COVID-19 restrictions. The key finding was that building rapport to tailor support was the most crucial aspect of practice, which workers could not adequately do without meeting face-to-face. Strengths-based practices, consisting of holistic, trauma-informed interactions, should become enshrined in reintegration job roles and the key performance indicators (KPIs) that measure success of the government contract.