.OTF font not being deployed to Azure

You probably need to configure the IIS to properly serve this file type. You do this by adding the following to the <system.webServer> element in Web.config:

<staticContent>    <mimeMap fileExtension=".otf" mimeType="font/otf" /></staticContent>

More infohttp://www.big.info/2013/06/how-to-use-otf-opentype-format-fonts-on.html

Place the following in web.config in the system.webServer configuration:

<system.webServer>       <staticContent>       <remove fileExtension=".otf" />       <mimeMap fileExtension=".otf" mimeType="font/otf" />    </staticContent></system.webServer>

HTTP Error 404 means the content is not found on server. It does mean that when you deploy your application to Windows Azure the content was not in the package.

As you suggested above that you do have .OTF set as content it means that you are asking compiler to treat it as static file and don't build it however specific file will not be copied to the final output folder to be the part of final CSPKG. You would need to set "Copy to output directory" as "copy always" so it can be part of CSPKG and deployed to Azure Cloud service.

Once you set file properties correctly and build your application, you can manually visit to your output folder to the verify that file is there as well as your CSPKG just by unzipping it.