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@spencergibb Just FYI, I ended up changing my approach to ensure that I'm on springboot 1.4.0.RELEASE and release train Brixton.SR5 and these two problems still exist.
TRACE aren't proxied through to the application and a
205 response still doesn't "finish" properly (i.e. it doesn't have a content-length or a chunk or a closed connection). I think the former is simply due to http://docs.spring.io/spring-framework/docs/4.3.x/spring-framework-reference/htmlsingle/#mvc-ann-requestmapping-head-options but the latter is unknown to me.
I've got a bit better handle on the code now so I'm hunting through, but if you've got any pointers, please feel free :)