I'm wondering if there is any way to get the Rails webserver (thin) to serve the *.gz files the asset pipeline creates. As I understand, those have a higher compression level than that of Rack::Deflater, which only works with serve_static_assets from within the rackup file and not in config.middleware.
A less optimal solution might be to change the default compression level of Zlib which is what Rack::Deflater references. It should only need to gzip once, then it goes to Rack::Cache, then hopefully a CDN.
A second less optimal solution might be a Rack::Rewrite.
The answer to your question can be found at https://gist.github.com/2152663.
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