A quick reminder to myself if I ever run into this problem: When using .less as css it might work fine when running thru Visual Studio but it fails with a 404 or a 406 when deploying to the IIS server. (ie. the CSS is not applied to the web page).
Probable solutions are here (404 - need to specify mime type) and here (406 - need to have consistent types).
Also should have IIS in Integrated Mode, not Classic if possible. Found this tip here
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