A system includes a processor and a memory comprising machine readable instructions that when executed by the processor, cause the system to receive command line instructions associated with execution of a Java virtual machine, the command line instructions associated with a set of rules for switching the Java virtual machine to a debugging mode, start execution of the Java virtual machine, start execution of an application on the Java virtual machine in a standard mode, during execution of the application, detecting an event that triggers a rule within the set of rules, and in response to the event, automatically switching the Java virtual machine from the standard mode to the debugging mode.