I have the following web.config:
After a lot of searching, I finally found what got compression working more consistently on my IIS 7.5. To start with, IIS will not compress a file unless it loaded often enough. That brings up the question "what does IIS consider often enough?" Well, the defaults are 2 times every 10 seconds. Yikes!
This setting can be changed in web.config, but the section needs to be unlocked first in applicationHost.config. Here are the commands:
First unlock the section:
C:\Windows\System32\inetsrv\appcmd.exe unlock config /section:system.webServer/serverRuntime
Unlocked section "system.webServer/serverRuntime" at configuration path "MACHINE/WEBROOT/APPHOST".
Now that is done, edit the web.config file
...
In this case, I set it to hit the file once in a 10 hour period. You can adjust the values as necessary. Here is the document that explains the serverRuntime element:
http://www.iis.net/configreference/system.webserver/serverruntime
I hope this helps get your compression working properly.