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Please file a new issue as I requested above. The behavior of workspace cleanup was completely rewritten in 1.551, so whatever's wrong in later versions is likely unrelated to this report.
That said, 1.569 is over half a year old and too old for new issue reports. I hope that's just a typo.
Make sure to create a log recorder for the logger hudson.model.WorkspaceCleanupThread on level ALL to find out what it actually does (https://wiki.jenkins-ci.org/display/JENKINS/Logging). "Deleted all workspaces" doesn't look like the cleanup thread's behavior at all.
Resolving as incomplete again.