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Currently, Any feature will display as shipping in the "NEXT UP" milestone on the roadmap as long as their entry is listed as shipping in that release. For each release, we have multiple features that end up not shipping in that milestone, and the features' shipping milestones are not expediently updated.
It might be useful to instead restrict the features that are displayed on the roadmap to only the ones that have API owner approval (for non-PSA features), since it should be nearly guaranteed that a shipped feature will obtain this approval.
This seems like a good idea to me, but I could have a knowledge gap here as to why this shouldn't be done.