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Update the workspace target to the RAP 1.4 M6 build version and run the UI Test Suite. The test mentioned above fails. Could this be related to changes in the underlying equinox bundles? Created an patch of WorkbenchStatusDialogManagerImpl that revive the test case and may help to find the cause of the problem.
Created attachment 193338 [details] WorkbenchStatusDialogManagerImpl that works around the problem
The Workbench UI test bundle is not maintained anymore. As this bug is very very old I will close it as WONTFIX.