I am implementing the bundling and minification support in MVC4 and setting it up so it can compile my Bootstrap .less files automatically for me. I have the following code in my BundleConfig.cs file
public class BundleConfig
{
    public static void RegisterBundles(BundleCollection bundles)
    {
        // base bundles that come with MVC 4
        var bootstrapBundle = new Bundle("~/bundles/bootstrap").Include("~/Content/less/bootstrap.less");
        bootstrapBundle.Transforms.Add(new TwitterBootstrapLessTransform());
        bootstrapBundle.Transforms.Add(new CssMinify());
        bundles.Add(bootstrapBundle);
    }
}
The TwitterBootsrapLessTransform is as follows (it is more complicated than I would like because of the need to import the sub .less files into dotLess)
public class TwitterBootstrapLessTransform : IBundleTransform
{
    public static string BundlePath { get; private set; }
    public void Process(BundleContext context, BundleResponse response)
    {
        setBasePath(context);
        var config = new DotlessConfiguration(DotlessConfiguration.GetDefault());
        config.LessSource = typeof(TwitterBootstrapLessMinifyBundleFileReader);
        response.Content = Less.Parse(response.Content, config);
        response.ContentType = "text/css";
    }
    private void setBasePath(BundleContext context)
    {
        BundlePath = context.HttpContext.Server.MapPath("~/Content/less" + "/imports" + "/");
    }
}
public class TwitterBootstrapLessMinifyBundleFileReader : IFileReader
{
    public IPathResolver PathResolver { get; set; }
    private string basePath;
    public TwitterBootstrapLessMinifyBundleFileReader(): this(new RelativePathResolver())
    {
    }
    public TwitterBootstrapLessMinifyBundleFileReader(IPathResolver pathResolver)
    {
        PathResolver = pathResolver;
        basePath = TwitterBootstrapLessTransform.BundlePath;
    }
    public bool DoesFileExist(string fileName)
    {
        fileName = PathResolver.GetFullPath(basePath + fileName);
        return File.Exists(fileName);
    }
    public byte[] GetBinaryFileContents(string fileName)
    {
        throw new System.NotImplementedException();
    }
    public string GetFileContents(string fileName)
    {
        fileName = PathResolver.GetFullPath(basePath + fileName);
        return File.ReadAllText(fileName);
    }
}
On my base _Layout.cshtml page I attempted to render the css files by doing this
@Styles.Render("~/bundles/bootstrap");
as is suggested by the mvc tutorial but the file the client browser ends up requesting is
http://localhost:53729/Content/less/bootstrap.less
which causes an error. If I put the following link into by base layout page it works as expected.
<link href="~/bundles/bootstrap" rel="stylesheet" type="text/css" />
Why isn't @Styles.Render() behaving in the same way in debug mode? It works in release mode. I can understand how you don't want it bundling and minifying in debug but how can I force this bundle to work the same way always?
So basically when debug="true", the Script/Style Render methods assume that Optimizations are off, meaning no bundling and no minification, which means it will not call into your transform; instead, it will just render out links to the raw contents of the bundle (Which is boostrap.less in your case).
You can override this behavior and always run optimization by setting BundleTable.EnableOptimizations = true.  This will force the render methods to always do bundling/minification.
What I ended up doing was putting a debug if statement in my _Layout.cshtml so the bundle would render no matter what. I'm not crazy about it as a solution but it is working for now.
@if (Context.IsDebuggingEnabled)
{
    <link href="~/bundles/bootstrap" rel="stylesheet" type="text/css" />
}
else
{
    @Styles.Render("~/bundles/bootstrap")
}
I get around this by letting dotless serve the .less file
in web.config:
   <handlers>
    <add name="dotless" path="*.less" verb="GET" type="dotless.Core.LessCssHttpHandler,dotless.Core" resourceType="File" preCondition="" />
    </handlers>
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