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A recently added feature blocks the deletion of duplicate targets, even by moderators. A user wishing to delete such a question is advised to reopen or delete the duplicates first.
Presumably, Community bot is not yet sentient enough to follow this advice. Does this mean that duplicate targets will never be automatically deleted?
They get deleted.
The dup-target restriction on voting to delete is just that: a restriction on voting. The abandoned-question cleanup doesn't vote; it just deletes.
We discussed this exact scenario while implementing the voting restriction, and identified the most likely scenario for auto-deletion of dup-targets as the one that matches your example: questions where the duplicate was asked by the author of the original. Why? Because in most other cases, dup-closing is restricted to targets that are answered, which also prevents auto-deletion.
Of course, leaving broken dup-links laying around isn't ideal, even in these situations - but the proper solution here lies elsewhere:
Neither of these are a very high priority right now (this is kind of an edge-case), so if you encounter these stubs laying around either vote to delete them or flag for moderator attention and let the mods know that the stub can safely be deleted as the target is gone.
We also discussed another, even more rare situation: a question closed as a duplicate of another question also closed as a duplicate, where the middle question in this chain gets deleted thus breaking the restriction on deleting the final target. This is... gonna be hard to fix in a robust manner; it would probably be more beneficial to simply create a list of edge-cases for mods and 10K users to review and sort out manually.
