Circle of Security-Parenting (COS-P) is a widely used parenting intervention that is gaining popularity globally as it is currently being delivered across several continents. Despite the global uptake of COS-P, there is limited research on its effectiveness with considerable variability in its delivery. Here we present a multi-site evaluation of the group delivery of COS-P to under-resourced mothers (n = 131 enrolled) in an urban community as facilitated by community-based providers (n = 12) from community sites (n = 6) that provide maternal and child services. The feasibility and acceptability of delivering COS-P in the community are highlighted as well as characteristics of sites and providers as they relate to implementation efforts, and pre and post-intervention data examining COS-P and maternal caregiving functioning (i.e., depressive symptoms, reflective functioning) are also included. Several service delivery barriers were encountered at agency, provider and participant levels that created obstacles for program dissemination, participant retention and evaluation. Nonetheless, COS-P was successfully delivered in the community when sites embedded the program within their existing infrastructure and had the internal capacity for delivery, participant recruitment, supervision, and community presence. Mothers who participated in COS-P also reported fewer depressive symptoms following the intervention (n = 25). This multi-site implementation and evaluation study has important implications for the delivery of parenting services to under-resourced communities globally. Implications for future research and service delivery are discussed.