Smart Groups not working with keywords?

I've gone through the various forum posts on Smart Groups (especially this one - http://discussions.apple.com/thread.jspa?messageID=8649078&#8649078) but still haven't found an answer to this problem.
After importing my test files into my local iTunes install, I used the "Get Info" method to edit the metadata for those files. At this time, I put a series of keywords in the "grouping" field. I then uploaded these test files to our iTunes U site.
When I search for those keywords on our site, I get the results that I expect to get. However, when I try to create a Smart Group based on any of those keywords, I get no results. I waited for a few days, hoping that the indexing would catch up and yield more search results - but that didn't seem to fix the problem. The documentation states that Smart Groups should work with keywords... so is there something I'm missing here?
Any thoughts would be very helpful.

Duncan, thanks for responding to me quickly.
I'm confused where the keyword field is, though. I don't know of a keyword field using the "Get Info" method of editing the file's metadata on the local iTunes install, and the guide is unclear about where that field is or how to add information into it.
On this page (http://deimos.apple.com/rsrc/doc/AppleEducation-iTunesUUsersGuide/UsingiTunesUSe arch/chapter10_section2.html), it mentions the following method for adding keywords for iTunes U:
"To add additional keywords for iTunes U to search:
1. Control-click the track where you want to add keywords, then choose Get Info from the shortcut menu that appears.
2. Click the Info tab.
3. Add keywords to the Grouping field. When searching your iTunes U site, after a track title, keywords in the Grouping field have the second-highest matching relevance.
4. Click OK."
This is the method that I've been using, since it seems to say that any words added to the "Grouping" field on the local install get read as keywords by iTunes U. Is there another way to add keywords to a file that I'm missing?

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