Robert,

What kind of filesystem is on /media/robert/Shared? It is likely that
/media/robert/Shared is a fat32, exfat, or NTFS filesystem. These
filesystems do not support posix permissions and therefore any attempt
to change the permissions/ownership will fail.

You stated that, "I know that the reported owner and group are lies ...
because if the owner were in fact root, I would not be able to create,
modify, and delete files as robert." Looking at your screenshot, it
appears that permissions for "Others" are set as "Create and delete
files". This grants any user on the system permission to create and
delete files (including robert).

Have you tried to reproduce the issue with files on /home/robert/ ?

Thanks

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https://bugs.launchpad.net/bugs/1830987

Title:
  Cannot change directory owner or group

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