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A large number of studies have focused on the neoliberal political and economic restructuring of non-profit immigrant settlement agencies (ISAs) through a policy analysis framework. While policy analysis is key to determining how resources are distributed among non-profit organizations, the challenges that ISAs encounter in planning and delivering services extend beyond limited financial resources in the sector. This research focuses on the system-level challenges ISAs encounter in planning and delivering services to newcomers in the suburban municipality of the Peel Region, Ontario, Canada. Twenty-one semi-structured interviews were conducted with frontline staff and executive directors in settlement organizations in Peel Region, Ontario, Canada, to understand the complex challenges they face within a highly federalized and neoliberal policy environment. The results indicate that although funding dollars are a large concern for ISAs, the conditions attached to funding, such as the types of programs settlement providers are able to offer, mandatory quotas, and restrictive eligibility criteria, hinder ISAs from being able to plan and implement programs that better respond to the needs of immigrants in Peel Region. The results also demonstrate that restrictive funding criteria contribute to competition with other ISAs for limited resources and challenge the structure and continuity of programs. Many of these challenges are exacerbated by the transportation system unique to suburban settings.