I've had the problem again and I can now reproduce it. It seems to come from a 
specific mix of root/user file access in subdirectories.
1. create a directory as simple user : mkdir testfolder1
2. inside this directory, create another one as root : sudo mkdir testfolder2
3. in that one, put a user file (you'll have to move it as root)
You then get the following structure : testfolder1 (user) -> testfolder2 (root) 
-> testfile1 (user)
Put testfolder1 in the trash and try to empty it from the context menu of the 
Gnome applet: you can't because of the folder with root access and you don't 
get an error message. Also, You can't move the content of the Trash elsewhere 
(with Nautilus), you'll have an error message related to access rights.

It seems that it's the combination of user inside root inside user
directory that triggers the bug.

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Trash applet : no warning when a file can't be deleted
https://bugs.launchpad.net/bugs/116564
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