Building on previous actor-to-actor perspectives in service systems, this study mapped the dialectic trajectory of actor role and identity transitions in the context of family caregiving. The study employed the theoretical lens of role and identity transitions and drew on in-depth, qualitative interviews with 22 unpaid family caregivers caring for dependent relatives to demonstrate how family caregiver roles and identities co-evolve throughout the caregiving journey. Our findings elucidate three dynamic reconfigurations of role and identity transitions in family caregiving. We evince how such transitions vary in both degree and type, and range from incremental to disruptive, as actors assume and detach from roles and associated identities. Theoretical contributions shed light on the emergent and nuanced nature of role and identity transitions, as roles and identities synchronously and asynchronously co-evolve in a service system in conjunction with changed relations between actors, society, and the service system. The paper concludes with implications for enhancing actor engagement in dynamic service systems.