Social mix has emerged as a consensus ‘top-down’ approach in urban policies throughout the Global North and beyond. In Ontario, Canada, the Growth Plan for the Greater Golden Horseshoe (2017) has legislated for urban growth centres (UGCs), which are existing or emerging downtowns like Downtown Oshawa, to achieve ‘balance’, ‘variety’, and/or ‘diversity’ by planning “complete communities”. In this context, Downtown Oshawa is undergoing a transition that resonates with post-revanchist understandings of contemporary gentrification. Specifically, local policies pledge to uphold ‘compassionate’ commitments to vulnerable populations while enticing relatively affluent newcomers. Informed by the theoretical framework of ‘everyday’ international political economy (EIPE), and adopting a critical realist grounded theory (CRGT) methodology, this qualitative case study set upon two objectives: (1) to determine if ‘everyday’ agents in Downtown Oshawa perceive ‘compassionate mix’ policies as legitimate; and (2) to establish what, if any, influence agents’ ‘bottom-up’ responses exerted. It contributes to extant literature by foregrounding the perceived policy legitimacy of non-elite agents and examining if and how their responses influenced practices and relations downtown. The results centre interviews (n = 25) with ‘everyday’ agents, or dwellers, who regularly spent time in Downtown Oshawa, as well as over 100 hours of observational fieldwork and a review of policies, legislation, and newspaper articles. Findings suggest that dwellers expressed a deep ambivalence captured by the EIPE concept of legitimation gaps. Specifically, dwellers endorsed local policies’ pledges to enhance the downtown reputation, import employment opportunities, and improve social control. However, rather than achieving these goals, dwellers experienced a variety of hardships associated with gentrification, including but not limited to a loss of place identity. Further, dwellers engaged in a variety of axiorational behaviours to compensate for perceived shortcomings in ‘compassionate’ service provisioning, including selective affiliation, holding ‘unconditional love’ and sustenance rallies for the vulnerable, and lending beds to others with insecure shelter. I situate these findings within broader academic discussions on resistance, gentrification, and poverty management before exploring alternative policy solutions to structurally address dwellers’ needs and frustrations.