My grandmother used to make cookies that looked like these every year for Christmas only she used a pecan instead of an m & m. They were my favorite. I’m not sure if this is the recipe or not. The cookie in this recipe seems to puff up more than hers did, but it tastes similar.
This recipe is one I adapted from Pillsbury to make the cookies gluten free with less sugar.

Base:

3/4 cup powdered sugar – I reduced this to 1/2 cup
3/4 cup butter, softened – I reduced this to 10 TBS since dough was sticky with full amount
2 tablespoons half and half
1 teaspoon vanilla
2 cups gluten free flour – I used 1 cup Bob’s Red Mill gluten free 1 to 1 Baking flour, 1 cup Bob’s Red Mill gluten free All purpose flour or just 2 cups gluten free 1 to 1 Baking flour

Filling:

21 caramels, unwrapped or 1 cup caramel bits
3 tablespoons half and half
3 tablespoons butter
3/4 cup powdered sugar – I used 1/2 cup powdered sugar

Glaze:

1/3 cup semisweet chocolate chips
1 tablespoon half and half
2 teaspoons butter
3 tablespoons powdered sugar – I used 2 tablespoons powdered sugar
1 teaspoon vanilla
red and green M & Ms

Combine all base ingredients except the flour. Slowly add the flour, mix well, wrap in plastic wrap and refrigerate 1 hour.

Heat oven to 325 F. Divide dough in half. Roll out and cut into squares/rectangles in desired sizes. If the dough is too sticky to roll out, just drop by 1/2 tablespoons onto a cookie sheet and flatten with a spoon. This is what I’ve done the past few years. They taste the same and it saves time.

Bake for 10 – 13 minutes. Remove from baking sheet and cool 15 minutes.

In a medium saucepan, combine the filling ingredients, except the powdered sugar. Cook over low heat until the caramel is melted and the mixture is smooth. Remove from the heat and add the powdered sugar. Spread 1 teaspoon of the filling over each cookie.

In a medium saucepan, combine the chocolate chips, half and half and butter. Cook over low heat until the chocolate chips are melted and the mixture is smooth. Remove from the heat and add the powdered sugar and vanilla. Spread over the caramel filling on each cookie. Top each cookie with an M & M.

This recipe made about 60 cookies when dropped with 1/2 tablespoon scoops onto a cookie sheet.

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