What is successful migration? At a macro-socio-political level migration by individuals may appear to be successful when it has met the objectives of governments, industries and domestic profit makers. However, delving beneath the surface can reveal contradictions and other measures of success at the individual, or micro-level. Within a broader critical historical ethnography, we interviewed 26 post-World War 2 (WW2) British migrants living in South Australia. All interviewees could be viewed as successful at the macro-level, having remained in Australia for many years and having established multi-generational Australian families. Their migration was a ‘success’ when measured against the priorities that were actively promoted by Australian governments in the post-WW2 period. At a micro-level, the migrants involved in this study reported mixed outcomes. While migration did result in self-identified aims of migration including employment, opportunities and adventure, some migrants reported high levels of distress and longing, linked to loss and dislocation from people and places in geographically distant locales. For some, these feelings extended into the present, raising questions over the ‘success’ of their migration experiences at a personal level. We argue that pro-active migration recruitment—such as that undertaken by Australian governments in the post-WW2 period—has the potential to pressure some persons into migration, creating ongoing and unresolvable tensions. Experiences of such disruptions merit further exploration to develop deeper critical understandings of migration success.