I managed to debug a Spring Boot application run with Gradle as a remote app in IntelliJ Idea. It’s not a very complicated setup, I just had to pass in additional JVM parameters when running the application with Gradle if I recall (and of course set up the remote debugging configuration in Idea). I know I’d also cry tears of joy if there was a more productive way of achieving that, but I think this is an issue between Jetbrains and Spring, not really a Gradle issue.