Problem:

I would say I debug a lot of the time but I am not really an expert on how to use the debugger tool to its full potential so there's some knowledge limitation to how I can use the debugger.

I was developing Java application and I used Jboss EAP for web server for my Java application to run but as I debug the application I always finish the debug by using the Run to caret position button and the breakpoint was never trigger ever again until I restart the server.

Solution to the problem:

This is my current version of IntelliJ Idea:

IntelliJ IDEA 2022.3.3 (Ultimate Edition)
Build #IU-223.8836.41, built on March 10, 2023
Runtime version: 17.0.6+1-b653.34 aarch64
VM: OpenJDK 64-Bit Server VM by JetBrains s.r.o.
macOS 13.4
Kotlin: 223-1.8.0-release-345-IJ8836.41

For you to hit the breakpoint as many time as you want, you would have to click on Resume Program Execution after your debug session. (Red Circle)

If you click on Run to where caret is, the debugger won't be able to re-hit the breakpoint again until you restart your server or application. (Red Circle)

Hope this help