I currently have both static and dynamic compression configured. The static compression is working, however the dynamic compression, when checked through YSlow and Fiddler,
Are you sure you have Dynamic Compression installed in IIS? By default, it is not installed on Server 2008 (or R2). Try this article: http://www.iis.net/ConfigReference/system.webServer/urlCompression
Check this thread, it sounds like you are having a similar issue:
How can I get gzip compression in IIS7 working?