Hi David,
Thanks for the detailed explanation.
In my tentative diagnostic I had forgotten about the keywords feature. If you do not want to resort to the radical solution of completely removing keywords from your glossary definitions, I suggest at least not entering keywords which appear in the definition of the entry being defined. In my experience, keywords can be very useful in language classes, but should be used sparingly. You might be interested in a "special" use of keywords for error correction, which I have explained in this discussion: Using Keywords Glossary feature for language "correction".
Joseph
PS.- Your screenshot does not show.
You have to attach it to your post (in the Attachment section at the bottom). Maybe if we can see that screenshot we will understand better what you call "mismatching".