I have a very simple project here https://github.com/sherry-ummen/javadebuggingnotworking
I am trying to get remote debugging working because I need it to do it for a similar case so I thought of trying it out with a simple one.
I have put a break point at line 12. Did maven build to create the jar and also set the remote debugging configuration to this 
And to start debugging I used the following command
java -Xdebug -Xrunjdwp:transport=dt_socket,address=8998,server=y -jar my-debug-test-0.0.1-SNAPSHOT.jar
Now when the process is listening , I go to IntelliJ and press remote debugging configuration then I get the following message on the Intellij output window without hitting the breakpoint.
Connected to the target VM, address: 'localhost:8998', transport: 'socket'
Disconnected from the target VM, address: 'localhost:8998', transport: 'socket'
And also in the console window where I started the java process gets stopped with the following message
C:\Users\sherry.ummen\eclipse-workspace\my-debug-test\target>java -Xdebug -
Xrunjdwp:transport=dt_socket,address=8998,server=y -jar my-debug-test-0.0.1-
SNAPSHOT.jar
Listening for transport dt_socket at address: 8998
no main manifest attribute, in my-debug-test-0.0.1-SNAPSHOT.jar
Now, I really do not understand why it behaves this way and I do not see my breakpoint hitting. It might be a very stupid question but I have very limited Java development skills so for me it's a headache.