Since you are on .NET, I recommend you check out the DotLess project . It is open source and very active. They have an HTTP handler that connects to IIS, it captures any request for the .less file and returns a valid CSS file. I don’t know how much caching they use, but you can probably rely on the browser to cache it enough.
The DotLess project also has an executable file that will be compiled whenever you want (for example, during the build of the project) or on demand.
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