Skilled labour shortages continue to challenge regional communities in Australia, whether for doctors and other health professionals, community and personal services workers, engineers, IT specialists or town planners. The COVID-19 pandemic exacerbated pre-existing shortages that were already apparent for many years. Attracting overseas trained skilled labour directly to regional areas is one strategy pursued by employers, including state and local governments in Australia. However, settlement challenges may be compounded by thin infrastructure and community services, cultural barriers and individual or family circumstances. This chapter utilises the multilevel intelligent career framework to analyse what support structures currently exist in regional Australia and if gaps need to be filled to ensure that: (1) skilled migrants can pursue careers in regional Australia; and (2) are likely to experience satisfying careers and settle long term in regional Australia. The framework covers micro, meso and macro level structures and processes related to societal, organisational, professional and person-to-person support systems that facilitate skilled migrants’ careers. It underscores the importance of both structures and individual agency in forging successful migrant careers in a host country such as Australia. Our analysis suggests the need to address micro- and meso-level structures to better support skilled migrants’ successful settlement in regional communities.