Actually, its not as much a Solr problem as a Lucene one, as it turns out, the WeightedSpanTermExtractor is in Lucene and not Solr.
Why they decided to only highlight queries that are in Lucene I don't know, but what I did to solve this problem was simply to make my queries extends a Lucene query instead of just "Query". So I decided to extend a BooleanQuery, which is the closest fit to what mine actually does. This make the highlighting "do something" even though its not perfect. Daniel Shane
