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If you hover over a button in the main toolbar (where new project, save, print,..., is displayed) and you cross one of the toolbar dividers the "show tooltip" status resets and you have to wait for the tooltips to be shown again. This does not have a large impact if there are not a lot of toolbars. However for first time users it can add frustration while trying to learn the product. This behaviour does not appear to happen on view specific toolbars (ie package explorer, and error log[from the plug-in development perspective]).
This is because of the drag bar. I don't believe there is anything that can be done, but I'll assign it to SWT to see if they wish to change how the cool bar works.
You are moving between coolitems in a coolbar when you move acroos the "separator". You are no longer in the same toolbar. This is OS behaviour. The same thing happens in Internet Explorer if you move between cool items. Closing as WONTIFIX.