Matthew,
what you describe sounds like the Turducken. Have a look at:
https://www.slideshare.net/RobertKeane1/turducken-divide-and-conquer-large-gwt-apps-with-multiple-teams
 
and
https://www.slideshare.net/gwtcon/diy-split-gwt-applications-using-turducken-approach-by-alberto-mancini

I vaguely remember Google Wave was done in GWT and had a plugin system: 
http://incubator.apache.org/projects/wave.html


On Friday, 14 September 2018 09:10:03 UTC-4, Matthew Bergshoeff wrote:
>
>  Hi Everyone - I've been searching everywhere for a solution to this and 
> haven't been able to resolve it. I don't think I've properly wrapped my 
> head around the issue, so hoping someone could provide some guidance.
>
> I am trying to build a modular GWT application - by that I mean that there 
> will be the core application, but it should support the addition of gwt 
> modules ("plugins") without having to rebuild. This is being accomplished 
> by updating parameters in the web.xml so that I can just stop the webapp, 
> add a .jar file to the /lib directory, define the new .jar in the web.xml 
> and restart the application. So far so good. The problem arises when trying 
> to initialize/access the classes within the plugins. 
>
> Let's imagine I had a PetStore application (classic example!). I have an 
> interface called *Pet* that is implemented by some classic examples (Cat, 
> Dog, Fish) in the core application. However, I want to be able to add a 
> plugin for an exotic pet (Borneo Pygmy Elephant), and have the application 
> (client-side) be able to load the class when a record comes up that refers 
> to it. I am able to do this server-side using a URLClassLoader, but can't 
> figure out how to use a Generator to instantiate all possible *Pet* 
> implementations within a module.
>
> If I am going to implement a generator, should it be in the plugin or in 
> the core application? I've found a few examples, but none seem to pinpoint 
> exactly what I'm trying to do. Appreciate any help...
>

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