Caramel-Filled Chocolate Cookies

By Alissa -
From: Culinary in the Country

I first found, and then lost, this recipe a couple of weeks ago. I really wanted to make them for our office party last week, where I have been taste-testing cookies for possible inclusion in our wedding cookie bar next year. After searching all the usual food blogs and not finding it again, I put out an SOS to Shannon, who found the recipe promptly. I think I missed it because I was looking for Rollo cookies, and the title clearly says "caramel-filled." At any rate, they were a big hit at work and at home, and I think will make it onto the cookie bar. The actual chocolate cookie isn't tremendously sweet, which works for me because I don't like super sweet things. This has more of a dark-chocolate flavor. I thought they were best just out of the oven while the caramel was still warm and gooey.

1 cup butter,softened
1 cup granulated sugar
1 cup packed brown sugar
2 eggs
2 teaspoons vanilla extract
2 1/2 cups all-purpose flour
1 teaspoon baking soda
3/4 cup unsweetened cocoa powder
2 tablespoons granulated sugar
48 Rollo candies (chocolate-covered caramels)

Beat butter until creamy. Gradually beat in white sugar and brown sugar. Beat in eggs and vanilla. Combine flour, baking soda and cocoa. Gradually add to butter mixture, beating well. Cover and chill at least 2 hours.

Preheat oven to 375 degrees F.

Divide the dough into 4 equal parts. Work with one part at a time, leaving the remainder in the refrigerator until needed. Divide each part into 12 pieces. Press each piece
of dough around a Rollo. Roll into a ball. Dip the tops gently into the granulated sugar. Place sugar side up, 2 inches apart on greased baking sheets.

Bake for 8 minutes in the preheated oven, rotating pan halfway at 4 minutes. Let cool for 4 minutes on the baking sheets before removing to wire racks to cool completely. If you try to take them off sooner the caramel might try to come out the bottom

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