Caramel Thumbprints with Chocolate Glaze (12 Weeks of Christmas Cookies)

Can you believe that Christmas is just around the corner???  Last year, I saw so many of my blogging friends participating in the 12 weeks of Christmas Cookies linky.  I was thrilled to find out how to join just in time this year.  Brenda over at Meal Planning Magic is hosting this event and you can still join in the fun.

I wanted to start out my series with a gloppy, decadent cookie.  After all, the holidays are the time to serve fancy, sugary treats.  Thumbprints are one of my family's favorite cookies.  Normally, I put jam in them, but this time, I filled the little wells with caramel and topped them off with a chocolate glaze.  I also switched out regular sugar for brown sugar, giving the cookies an extra butterscotch flavor.

Caramel Thumbprints with Chocolate Glaze:
for the cookie
1/2 cup butter (1 stick), at room temperature
1/2 cup brown sugar
1 egg
1 1/2 tsp vanilla
2 cups flour
for the filling
14 caramels
1 1/2 Tbsp milk
for the glaze
1/3 cup chocolate chips
1 tsp shortening
Cream the butter and brown sugar.  Add the egg and vanilla, mix thoroughly, scraping down the bowl.  Add the flour and mix well.  Place teaspoon sized balls of dough onto a cookie sheet.  Make an indentation with your thumb and bake in a preheated 375 degree oven for 8 minutes.  Cool on a rack.  Place caramels and milk in a small microwavable bowl and heat for 1 minute.  Stir until smooth.  (If not completely smooth, heat for another 30 seconds and stir).  Spoon 1/2 teaspoon filling into each cookie dent.  In another small bowl, microwave the chocolate chips and shortening.  Stir until smooth and then spoon into a plastic bag.  Cut a tiny hole in one of the corners and pipe the glaze over the cookies in a swooshing motion.  Let sit for at least 20 minutes before serving to set (and to cool because that filling will be quite hot).

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