Refugees may struggle to overcome not only psychological impacts of pre-resettlement events but also additional living challenges in post-resettlement contexts. This study aims to understand how context-specific factors influence the psychosocial wellbeing of Syrian refugees through comparing difficulties and resources in two locations. A total of 185 Syrians (Buffalo N = 82, Istanbul N = 103) completed various measures. The Istanbul sample was more educated and employed, had been in Turkey for a longer time, had less monthly income, and experience more discrimination than the sample in Buffalo. Post-migration living difficulties and the satisfaction with quality of life made unique contributions to mental health in both samples. Identifying key contextual factors in the place refugees live contributed to a multifaceted understanding of their experiences and how those experiences impact their mental health and psychosocial wellbeing. Studying post-resettlement contexts can facilitate the development of interventions, programs, and policies that address the needs of refugees. Future studies with Syrian refugees may take into consideration cultural elements identified through this study in order to develop culturally congruent practices and research. Future research should identify the challenges of sub-groups (e.g., single or widowed individuals) within Syrian refugees to achieve social justice for every member of this population.