Commented Unassigned: Font not used when rendering image on server [9044]

For some reason, the font I've defined in my css is not being used when rendering an image on my server. It works fine locally. I've verified that the font is installed on the server.

Is there anything else that I should be doing? Not really sure how to troubleshoot this. Any help would be appreciated.
Comments: I agree its a Windows issue, great you found it.