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Created attachment 235192 [details] Screenshot The attached example is one the GEF Examples with the only difference that the 2 figures have tooltips. Steps to reproduce: 1. start the plugin and open the shape editor 2. create a figure and open its tooltip 3. detach the editor 4. open the tooltip a the figure again Sometimes it does not happen at the first try.
Created attachment 235193 [details] Example
Created attachment 256614 [details] Patch that recreates PopupHelper's LWS/Shell on parent Shell change To me the root of the problem seems to be the cached Shell and LightweightSystem in Draw2D's PopUpHelper. When you detach the editor, the parent-Shell of the popup-Shell should be the new detached Shell, but it still is the initial Shell, usually the workbench-window, which I think causes the in-between ToolTip. Also, if you detach first, show the tooltip, re-attach and try to show the tooltip, you get an exception. I attached a patch which looks for parent shell changes and invalidates cached Shell and LWS in this case. Users of the changed methods now have to deal with the possibility that getShell() and getLightweightSystem() may return different Objects on successive calls, don't know if that is acceptable for API.