Rolo cookie cups have a melting Rolo middle and soft brownie cookie cup shell, ready in just 15 minutes.

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Day 3 of the 12 days of Christmas: Rolo Cookie Cups

My family has their traditional Christmas cookies that we make every year. From Italian Anise Cookies to Pizzelles, we have this cookie making business down pat. But those aren’t the only cookies we make on our annual Cookie Day.

Another family favorite is Rolo Cookie Cups. I am not sure when we started making these but everyone looks forward to them as much as the Italian Anise Cookies.  My mom found this recipe in an old cookbook (and I wish I knew the name!) and have become a staple to our Christmas baking extravaganza. While we wait for the Anise cookies to cool, we whip up 4 batches (yeah, four!).

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The only hard part to this recipe? Keeping people from eating the unwrapped Rolos while we wait for the cookies to bake! Someone, every year, will sneak a Rolo and we will be short one. Never fails!

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Rolo Cookie Cups

For this recipe, you will need a mini muffin tin and paper liners. And don’t forget the Rolos!

Rolo Cookie Cups

Ingredients

  • 1 stick of butter, softened
  • 1 cup sugar
  • 2 eggs
  • 2 oz unsweetened chocolate, melted
  • 1 tsp vanilla
  • 1/2 tsp salt
  • 1 cup flour
  • 36 unwrapped Rolos

Instructions

  1. Soften butter and melt chocolate.
  2. Mix all ingredients in mixer.
  3. Using a teaspoon, fill small muffin tins with paper liners.
  4. Bakes at 350 for 10-12 minutes.
  5. Remove from oven and immediately add Rolos to center of cookie cups (upside down).
  6. Cool on wire racks for 10 minutes before removing from muffin tin.

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WANT MORE CHRISTMAS COOKIE RECIPES? YOU CAN FIND THEM ALL HERE!

 

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