Is there a way I can make the compiler print more details instead of only Stack overflow message ?
The GWT Compiler has a -logLevel parameter but I am unsure if there is that much logging going on while figuring out serialization information.
And is there a way to debug the compiler while its in action in my project ?
Sure the GWT compiler is just a Java process so you can remote debug it as any other Java process by launching it in debug mode and connect to it using your IDE of choice.
You could also try using -draftCompile or -optimize 8 to see if it makes a difference. Sometimes -optimize 9 does never complete compiling because it optimizes in an endless loop and aborts as soon as the AST of your code does not change anymore. Sometimes that simply never happens. A number smaller than 9 defines the max optimization passes.
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