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Anna Pham

Smiley Face Cookies

Using only 11 ingredients make these soft vanilla-almond flavored cookies with a hardened glaze icing. I recommend chilling the cookie dough for 30 minutes to an hour before forming the cookies.
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Prep Time 1 hour
Cook Time 15 minutes
Chill Time 1 hour
Total Time 2 hours 15 minutes
Servings: 20 cookies
Course: Dessert
Calories: 269
Ingredients Equipment Method

Ingredients
  

Cookie Dough
  • 1 Cup Unsalted Butter Room Temperature
  • 3/4 Cup Granulated Sugar
  • 1 1/2 Tsp Vanilla Extract
  • 1 Tsp Almond Extract
  • 1 Large Egg
  • 2 1/4 Cups All Purpose Flour
  • 1/2 Tsp Salt
  • 2 Tbsp Milk I use Whole Milk but you can substitute if needed.
Icing
  • 6 Cups Confectioners Sugar
  • 1 Tsp Vanilla Extract
  • 1 Tsp Almond Extract
  • 4 Tsp Light Corn Syrup
  • 8-10 Tbsp Water Room Temperature
  • pinch Salt
  • Food Coloring Red and Yellow
Chocolate Icing
  • 4 Squares 60% Cacao Bittersweet Chocolate I use the Ghirardelli Premium Baking Bars.
  • Water As needed

Equipment

  • 1 Stand Mixer
  • 1 Paddle Attachment
  • 1 Whisk Attachment
  • 2 Parchment Paper
  • 1 Plastic Wrap
  • 1 Piping Bag or Squeeze Bottle
  • 2 Baking Sheets
  • 1-2 Cooling Racks
  • 1 Large Measuring Cup
  • 1 Toothpick

Method
 

  1. Read through the recipe completely prior to beginning. Make room in your refrigerator to put your dough in to chill for 30 minutes-an hour. Without chilling the dough will over-spread and won't hold it's shape. This recipe involves an icing that needs time to set and harden, prepare to leave cookies uncovered to harden for 8-12 hours OR you can speed this time by putting in the oven at 100 °F for 1-2 hours.
Make the cookie dough:
  1. In a Stand Mixer with a Paddle Attachment beat the butter and granulated Sugar until creamy on a medium/high speed (~2 minutes). Add in the egg, vanilla extract, and almond extract, and beat on high speed until combined (~1 minute). Scrape down the sides and up the bottom of the bowl and beat again as needed to combine.
    1 Cup Unsalted Butter, 3/4 Cup Granulated Sugar, 1 1/2 Tsp Vanilla Extract, 1 Tsp Almond Extract, 1 Large Egg
  2. On a low speed, slowly beat in the flour and salt. Turn up to a high speed and beat until completely combined. On a medium speed, beat in 2 Tablespoons of milk. You want a dough that's creamy but still thick. The milk makes the chilling imperative so the cookies do not over-spread.
    2 1/4 Cups All Purpose Flour, 1/2 Tsp Salt, 2 Tbsp Milk
  3. Set out some Plastic Wrap and spoon your dough onto it. Wrap it and flatten it until it is roughly 1 inch in thickness. Put wrapped dough into fridge to chill for about an hour.
  4. Remove dough from fridge and preheat oven to 350 °F
  5. Grab 2 large Baking Sheets and line with Parchment Paper. Roll dough balls about 2 Tablespoons in size. Use something with a flat bottom (I use a large measuring cup) to press down the dough balls until they are roughly 1/4 inch thick.
  6. Put cookies into the oven and bake for 13-15 minutes, swapping trays halfway to ensure they cook evenly. You want the cookies to be soft but firm. Once cookies are done baking, let them chill on the trays for 5 minutes before transferring to Cooling Racks to cool completely before icing.
Make the icing:
  1. In a Stand Mixer fit with a Whisk Attachment mix together the confectioners sugar, vanilla extract, almond extract, salt, and corn syrup. Add water (start with 5 Tablespoons, mix, then add 1 Tablespoon at a time until you reach the desired consistency). You want to be able to drizzle the icing off the whisk and it sit on top for a few seconds before melting back into the rest of the icing.
    6 Cups Confectioners Sugar, 1 Tsp Vanilla Extract, 1 Tsp Almond Extract, 4 Tsp Light Corn Syrup, 8-10 Tbsp Water, pinch Salt, Food Coloring
  2. Once you have the icing the desired consistency, add in the red and yellow Food Coloring. Start with 10 drops of the yellow and 12 drops of the red. Mix and add more of each until you reach your desired orange color.
Icing the cookies:
  1. To ice the cookies, I place them on a Cooling Rack on top of the Parchment Paper that I baked them on to catch the run off icing. I transfer the icing from the Stand Mixer into a Large Measuring Cup (you can use an alternative if needed) with a spout and slowly pour the icing over each cookie.
  2. After pouring the icing I go back with a Toothpick and pull the icing to any spots that didn't get covered on the cookies.
  3. Scrape any excess icing off the Parchment Paper and put back into the Large Measuring Cup to use for the chocolate icing.
  4. Put in the oven at 100 °F to harden while we make the chocolate icing.
Make the chocolate icing:
  1. To make the chocolate icing, I melt 4 squares of chocolate and mix it into the remaining orange icing. Add a small amount of water to thin icing out.
    4 Squares 60% Cacao Bittersweet Chocolate, Water
  2. Put the chocolate icing into a Piping Bag or other container you use to decorate with. (I use a squeeze bottle).
Make the Smiley Face:
  1. Once you have finished mixing together the chocolate icing, remove the cookies from the oven and begin drawing the faces on each cookie however you like.
  2. Once finished drawing the Smiles, put finished cookies back into the oven at 100 °F for 1-2 hours to set the icing.
  3. Cookies stay fresh in an airtight container at room temperature for up to 1 week.