Even with "stoptimeout" set, the ShutDownHook is never run when the service is stopped. The ShutDownHook does run if the Java application throws an uncaught exception.

Log is

2018-07-01 19:33:23,134 INFO - Stopping DRS IDB DEV Test 2018-07-01 19:33:23,149 DEBUG - ProcessKill 8732 2018-07-01 19:33:23,250 INFO - Found child process: 7420 Name: conhost.exe 2018-07-01 19:33:23,290 INFO - Stopping process 7420 2018-07-01 19:33:23,309 INFO - Send SIGINT 7420 2018-07-01 19:33:23,314 WARN - SIGINT to 7420 failed - Killing as fallback 2018-07-01 19:33:23,324 INFO - Stopping process 8732 2018-07-01 19:33:23,334 INFO - Send SIGINT 8732 2018-07-01 19:33:23,339 WARN - SIGINT to 8732 failed - Killing as fallback 2018-07-01 19:33:23,344 INFO - Finished DRS IDB DEV Test 2018-07-01 19:33:23,354 DEBUG - Completed. Exit code is 0

Code is