The COVID-19 pandemic altered global migration, reducing skilled immigrants to Canada in 2020-2021. In response, the federal government raised immigration targets and implemented policy changes, such as the two-step immigration model to tackle labour shortages. However, this coincided with increasing domestic crises in housing, healthcare, and cost of living. Barriers such as credential devaluation and underemployment have raised concerns about skilled immigrants’ dissatisfaction and migration trends. This research examines the relationship between pre- and post-migration experiences and their effect on retention or onward migration decisions, alongside the emotional attachment immigrants form to their new homes. Focusing on the Ottawa-Gatineau area, this study looks at the experiences of bilingual skilled immigrants facing unique local dynamics. Using a combined framework of aspirations-capabilities, social resilience, and emotional geography, it seeks to understand how structural inequities intersect with identity markers—such as race, gender, and language, affecting integration. Emotional geography sheds light on how feelings of belonging are linked to place-based elements— bilingualism policies and job opportunities. Using a qualitative case study approach, semi-structured interviews with skilled immigrants (permanent residents and temporary migrants) and key informants from government and community organizations provide insights into settlement challenges, institutional support gaps, emotional connections to place, and policy impacts. Unmet expectations regarding economic opportunities lead to disillusionment, yet emotional ties to place, driven by social networks and cultural involvement, play a vital role in retention. This research informs Canada’s immigration strategies by identifying strengths and weaknesses in talent retention amid global challenges and recommends enhancements for inclusivity and long-term retention efforts for skilled immigrants, addressing systemic barriers affecting their connection to Canada.