Originally Posted by KHalstead
Here's the thing with chocolate and chocolate candies........the chocolate candies like hershey's kisses, etc. are all tempered chocolate. Meaning it has been raised to a certain temperature and then cooled and raised and cooled (however the process goes) so that it WILL resolidify once it cools again.
Sorry to get all technical, but tempered chocolate only remains tempered until it's heated. If you take a tempered piece of REAL chocolate and heat it (either through baking or other means) it will lose temper. Will it resolidify somewhat? Yes, but it will never completely reset to temper and it will be softer then it was before. Hershey's kisses--while they are real chocolate--also have other additives to help them hold their shape even when they get warm/hot and re-cool, although even then they won't complete reset perfectly.
Good, high quality, pure chocolate is always sold tempered and must be tempered anytime it is re-melted and used That is the reason it will stay soft if you bake it in the middle of something, because it will fall out of temper through the baking process and it doesn't have the added stable fats that many commercial chocolates (like hershey does) to help it stay in a tempered-like state.
As far as the original question goes, you'll have better luck with a filled candy (like a mini peanut butter cup) so it's not a solid lump of chocolate and it will remain somewhat soft after baking.