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I've configured IIS to act as a reverse proxy for a development server (dartlang's pub serve if you're curious). I'm doing this because the development server doesn't support custom error pages and I need them to be working locally. I've set up the custom error page in IIS but it's not serving it -- it's passing through the default 404 page from the source server. Is it possible to make the reverse proxy serve it's own custom page for 404 errors?

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Late to the party, but here you go: when using IIS 7+ as a reverse proxy, you can configure it to use its own error pages (custom or otherwise) by adding the following to web.config:

<system.webServer> <httpErrors existingResponse="Replace"/> </system.webServer> 

More info in the docs...

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