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When I first open my work space and click a project in the Project Explorer, and use alt-shift-X, B nothing happens. But after I right click open the context menu, it works. It looks like the shortcuts are loaded only after a user "activates" the menu or something.
Could you please try the following steps (without opening context menus): 1. open your workspace 2. switch to debug perspective 3. optional switch back to your start perspective 4. start your project with Alt+Shift+X, B Same result? Beside are you sure the project is not started or just not visible. I suspect this is related to bug 239217.
Found time to test it myself. The project indeed does not start if Alt+Shift+X, B is used and org.eclipse.debug.ui plug-in is not loaded. This seem to be limited for this specific shortcut family. Starting the spring boot app from Boot Dashboard works even before debug.ui plug-in is loaded. And most important it is not a spring specific problem. I can reproduce the same problem with Alt+Shift+X, J to run a Java application.
Bug 218881 came up which is the same problem as this one. I've added the progress I made working on this (not much) in bug 218881 comment 28. *** This bug has been marked as a duplicate of bug 218881 ***