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Currently this answer is shown as being a community wiki post. There's no reason for it to be, so someone (not me) tried to remove the community wiki status of the post. This was logged in the timeline, which currently says:

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There's no mention of it being 'made wiki' again after that. According to this post and science done by Ryan M and Andrew T., that is probably because re-adding the community wiki status doesn't create another timeline entry.

This is confusing, since I was thinking the button may have malfunctioned (see my first revision). Can this please be fixed, so moderators can know what happened and can act accordingly?

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It looks like the bug is that after the first instance of adding and removing Community Wiki status, additional Timeline entries aren't generated.

In order to reproduce the bug, this (now deleted) post was converted to and from Community Wiki three times each (simulating a "war" between a user and a moderator over a post's Community Wiki status) with the assistance of a helpful moderator. However, only the first conversion each way shows up, despite edits and comments occurring in between:

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