In the context of youth offending, restorative justice (RJ) is well-established in Australia and New Zealand, and research has established clear benefits of RJ for victims and offenders. On the other hand, RJ also faces substantial roadblocks or challenges that are frequently overlooked in scholarly research on Australia and New Zealand, and there are tensions or fault lines between its use in “mainstream” youth and adult justice practices, and its use outside of the criminal justice system. Our chapter looks at these challenges on two levels—macro (i.e. political and social structural), meso (i.e. institutional, community, and group). Within these levels we also discuss how such challenges are in turn informing problems, changes, and innovations at the level of practice. We explicate these roadblocks in the context of issues specific to Australia and Aotearoa/New Zealand, but also comparatively in terms of similar issues faced by restorative justice in other western jurisdictions. We conclude with discussion of how these challenges may or may not be resolved in terms of possible trajectories for restorative justice in both countries and the restorative movement more broadly.