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A directory and a file in it which were both created and deleted lately were checked out into a working copy that was not updated for a long while.
So, I assume that there is a problem, if both, the creation and the deletion were not yet synced. The actual data is of course still in the history, so it is technically possible to check it out. But it should be marked as "deleted" and it should not be in the change-set fetched from the server.