Hot Swap Content in Jars Loaded Using JVM arguments?

I have a Spring Boot (1.5) application that implements a poor man's plugin system by loading a set of jars at runtime from a known location using the -Dloader.path VM argument when starting the primary application jar.

While this works as expected in production but there are some serious workflow problems when it comes to seeing changes in the plugin jars loaded at runtime. Seeing any changes in these jars requires shutdown/restart of the host application jar and manual replacement of the updated plugin jar, so i'd like to figure out if there's a way to implement hot swapping for a jar loaded at runtime. I'm guessing my setup is non-standard enough to not allow it, but i figured i'd ask.