404 errors in IIS7 for embedded .woff font files08/16/2011
All contemporary browsers support embedding custom fonts to the web pages. The best free online tool to assist the developer with generating required font files and CSS rules is Font Squirrel's @Font-face generator (http://www.fontsquirrel.com/fontface/generator). The tool will let you upload your custom font file in any format and download back the CSS rules and all necessary font formats to be fully cross-browser compatible (.eot, .woff, .ttf, and .svg).
After using this tool to embed custom fonts into a website I noticed I was getting 404 errors from references to the font.woff file. After some troubleshooting, I noticed IIS7 does not recognize .woff file's mime type by default.
To solve the problem, double-click the "MIME Types" configuration option while having IIS root node selected in the left panel and click "Add..." link in the Actions panel on the right. This will bring up the following dialog. Add .woff file extension and specify "application/x-font-woff" as the corresponding MIME type:
Add MIME Type for .woff file name extension
This will force IIS to process .woff files correctly and will fix 404 errors associated with these files.