Thanks.... unfortunately there is not a single indication in the log
file that anything went wrong... weird.

Can you try the following as well when the bug occurs: After clearing
the history if the menu doesn't not update, copy another item to the
clipboard and check the clipboard menu again whether this content has
been added.

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https://bugs.launchpad.net/bugs/1383013

Title:
  Diodon on 14.10 does not clear history consistently

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