Preheat the oven to 350 degrees F. Line cookie sheets with parchment paper or silpat mats (or spray with nonstick spray).
Use an electric mixer and a large bowl to combine the butter and sugar. Beat in the egg and extract, then chocolate. Add the flour and mix until combined.
Shape into 1-inch balls. Place the dough balls on a cookie sheet 2-inches apart, and make a thumbprint in each ball. Bake for 8 to 10 minutes, or until cooked through and not super soft
When you take them out of the oven, use a small spoon to press down slightly into the thumbprinted areas again to make sure each cookie has a nice impression. Cool.
Melt caramels in a double boiler. Stir in the half and half until well combined and smooth. Spoon a little bit of the caramel mixture into each cookie imprint. Top with a pecan half.
Notes
These cookies will be more chocolatey with chocolate extract, which can be found in specialty markets like Whole Foods