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Using Tomcat 8.5.15 or 8.5.16 the debugger IDE buttons (Finish, Pause, Continue, Single-Step etc.) remain grayed out even though the application is successfully deployed, server started and the debugger is actually attached. Once a breakpoint is hit, the debugger correctly stops and the GUI is updated accordingly. This happens only at the second and further attempts to debug a web application. When NB is freshly started, the first debugger session behaves correctly. The incorrect behavior starts once the first debugging session is finished.