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The Best Boozy Holiday Chocolate Kiss Cookies!

The Best Boozy Holiday Chocolate Kiss Cookies!

By Mona - Far From The Farm
October 14, 2025
Soft, chewy Bailey’s cookies filled with chocolate kisses and cozy holiday flavor - perfect for grown-up celebrations! 
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Makes: 24 large cookies
Approximate cost $10
Prep Time 20 minutes
Cook Time 15 minutes
Chill time 1 hour
Total Time 1 hour 35 minutes
Servings: 24 large cookies
Course: Cookies, Dessert
Cuisine: American

Ingredients
  

  • 2 & ¾ cups All-purpose flour
  • ¾ tsp Salt
  • 1 tsp Baking soda
  • 1 tsp Instant coffee granules - or espresso powder
  • 1 cup Butter, softened - salted or unsalted, to your preference
  • 1 cup Packed brown sugar
  • ½ cup White granulated sugar
  • 2 tsp Vanilla
  • ¼ cup 2 & ¼ cups Hershey Kisses, unwrapped - or store brand equivalent
  • 2 Large eggs

Equipment

  • Stand mixer or hand mixer
  • mixing bowls
  • spatula
  • Measuring cups, spoons and a jug
  • baking sheets
  • Parchment paper
  • cookie scoop
  • cooling rack
  • Plastic wrap for chilling dough

Method
 

  1. Combine dry ingredients. In a bowl, whisk together the flour, salt, baking soda, and instant coffee granules. Set aside.
  2. Cream butter and sugars. In the bowl of a stand mixer, beat butter, brown sugar, and white sugar for about 2 minutes until fluffy.
  3. Add flavor and liquid. Turn the mixer to low and slowly pour in the Bailey’s and vanilla extract until just combined.
  4. Mix in eggs. Add the eggs one at a time, beating until smooth.
  5. Fold in dry mix. Remove from the mixer and gently fold in the dry ingredients, about half a cup at a time, until no dry spots remain.
  6. Add chocolate. Stir in the Hershey Kisses until evenly distributed.
  7. Chill dough. Cover the bowl with plastic wrap and chill in the fridge for at least 1 hour but preferably overnight.
  8. Bake. Preheat oven to 375°F and line a baking sheet with parchment paper. Scoop large mounds (about 3 tablespoons each) spaced evenly apart. Bake 10–12 minutes until golden at the edges.
  9. Cool. Let cookies rest on the sheet for 5 minutes before transferring to a wire rack to cool completely.

Video

Notes

 
  • The Bailey’s flavor is light and blends with the coffee beautifully - you can adjust up or down to taste.
  • If using different chocolates, chop them roughly for that chunky, gooey texture.
 

Storage

Keep in an airtight container at room temperature up to 4 days. For longer storage, freeze in a sealed bag for up to 2 months and thaw on the counter before serving.
 
 

Nutrition information is automatically calculated, so should only be used as an approximation.