Bubbling up newest content in lucene search results

For debugging Lucene, the best tool to use is Luke, which lets you poke around in the index itself to see what got indexed, carry out searches, etc. I recommend downloading it, pointing it at your index, and seeing what's in there.

You can use phrase + slop as bajafresh4life says, but it will fail to match anything if the terms are more than slop apart.

A slightly more complicated alternative is to construct a boolean query that explicitly searches for the phrase (with or without slop) and each of the terms in the phrase. E.g.

"healthcare insurance" OR healthcare OR insurance

Normal lucene relevance sort will give you what you want, and won't fail in the way that the "big slop" approach will.

You can also boost individual fields so that, for example, title is weighted more heavily than description or company name. This needs an even more complicated query, but gives you a lot more control over the ordering...

title:"healthcare insurance"^2 OR title:healthcare^2 OR title:insurance^2
OR description:"healthcare insurance" OR ...

It can be quite tricky to get the weights right, and you may have to play around with them to get exactly what you want (e.g. in the example I just gave, you might not want to boost the individual terms for title), but when you get it working, its pretty nice :-)