Chocolate Dipped Strawberry Cookie

10 mins
Serves 14
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Directions

  1. 1Pour 1 cup of whole milk into a bowl.
  2. 2Pour 1 cup of whole milk into a bowl.
  3. 3Pour 1 cup of whole milk into a bowl.
  4. 4Add 1 box of vanilla pudding mix to the milk.
  5. 5Add 1 box of vanilla pudding mix to the milk.
  6. 6Add 1 box of vanilla pudding mix to the milk.
  7. 7Whisk the vanilla pudding mix into the milk until it thickens up.
  8. 8Whisk the vanilla pudding mix into the milk until it thickens up.
  9. 9Whisk the vanilla pudding mix into the milk until it thickens up.
  10. 10Add 2 teaspoons of strawberry extract to the thickened pudding mix.
  11. 11Add 2 teaspoons of strawberry extract to the thickened pudding mix.
  12. 12Add 2 teaspoons of strawberry extract to the thickened pudding mix.
  13. 13Add 2 cups of diced frozen (unthawed) strawberries to the pudding mix.
  14. 14Add 2 cups of diced frozen (unthawed) strawberries to the pudding mix.
  15. 15Add 2 cups of diced frozen (unthawed) strawberries to the pudding mix.
  16. 16Add 8 oz of Cool Whip to the pudding mix.
  17. 17Add 8 oz of Cool Whip to the pudding mix.
  18. 18Add 8 oz of Cool Whip to the pudding mix.
  19. 19Fold all the ingredients together with a spatula until fully combined.
  20. 20Fold all the ingredients together with a spatula until fully combined.
  21. 21Fold all the ingredients together with a spatula until fully combined.
  22. 22Place the strawberry pudding in the fridge to chill.
  23. 23Place the strawberry pudding in the fridge to chill.
  24. 24Place the strawberry pudding in the fridge to chill.
  25. 25Combine 4 1/2 cups of all-purpose flour, 1 cup of cocoa powder, 1 teaspoon of salt, 1/2 teaspoon of baking soda, and 1/2 teaspoon of cream of tartar in a separate bowl.
  26. 26Combine 4 1/2 cups of all-purpose flour, 1 cup of cocoa powder, 1 teaspoon of salt, 1/2 teaspoon of baking soda, and 1/2 teaspoon of cream of tartar in a separate bowl.
  27. 27Combine 4 1/2 cups of all-purpose flour, 1 cup of cocoa powder, 1 teaspoon of salt, 1/2 teaspoon of baking soda, and 1/2 teaspoon of cream of tartar in a separate bowl.
  28. 28Whisk the dry ingredients together and set aside.
  29. 29Whisk the dry ingredients together and set aside.
  30. 30Whisk the dry ingredients together and set aside.
  31. 31Combine 1 cup of softened unsalted butter with 1 1/3 cups of granulated sugar and 3/4 cup of powdered sugar in a bowl.
  32. 32Combine 1 cup of softened unsalted butter with 1 1/3 cups of granulated sugar and 3/4 cup of powdered sugar in a bowl.
  33. 33Combine 1 cup of softened unsalted butter with 1 1/3 cups of granulated sugar and 3/4 cup of powdered sugar in a bowl.
  34. 34Whisk the butter and sugars until creamy and smooth.
  35. 35Whisk the butter and sugars until creamy and smooth.
  36. 36Whisk the butter and sugars until creamy and smooth.
  37. 37Add 3/4 cup of vegetable oil, 2 large room temperature eggs, and 1 tablespoon of water to the creamy mixture.
  38. 38Add 3/4 cup of vegetable oil, 2 large room temperature eggs, and 1 tablespoon of water to the creamy mixture.
  39. 39Add 3/4 cup of vegetable oil, 2 large room temperature eggs, and 1 tablespoon of water to the creamy mixture.
  40. 40Whisk the wet ingredients until fully combined.
  41. 41Whisk the wet ingredients until fully combined.
  42. 42Whisk the wet ingredients until fully combined.
  43. 43Fold in the dry ingredients into the wet mixture until the dough comes together.
  44. 44Fold in the dry ingredients into the wet mixture until the dough comes together.
  45. 45Fold in the dry ingredients into the wet mixture until the dough comes together.
  46. 46Scoop out 14 equal-sized cookie dough balls.
  47. 47Scoop out 14 equal-sized cookie dough balls.
  48. 48Scoop out 14 equal-sized cookie dough balls.
  49. 49Place the cookie dough balls on a baking sheet lined with parchment paper.
  50. 50Place the cookie dough balls on a baking sheet lined with parchment paper.
  51. 51Place the cookie dough balls on a baking sheet lined with parchment paper.
  52. 52Use a round object or cookie cutter to make a pocket in the middle of each cookie dough ball before baking.
  53. 53Use a round object or cookie cutter to make a pocket in the middle of each cookie dough ball before baking.
  54. 54Use a round object or cookie cutter to make a pocket in the middle of each cookie dough ball before baking.
  55. 55Bake the cookies at 350 degrees Fahrenheit for 10 to 12 minutes.
  56. 56Bake the cookies at 350 degrees Fahrenheit for 10 to 12 minutes.
  57. 57Bake the cookies at 350 degrees Fahrenheit for 10 to 12 minutes.
  58. 58While the cookies are baking, slice fresh strawberries.
  59. 59While the cookies are baking, slice fresh strawberries.
  60. 60While the cookies are baking, slice fresh strawberries.
  61. 61Melt chocolate for topping.
  62. 62Melt chocolate for topping.
  63. 63Melt chocolate for topping.
  64. 64Once the cookies have cooled down, fill the pockets with the chilled strawberry pudding.
  65. 65Once the cookies have cooled down, fill the pockets with the chilled strawberry pudding.
  66. 66Once the cookies have cooled down, fill the pockets with the chilled strawberry pudding.
  67. 67Drizzle melted chocolate over the pudding on each cookie.
  68. 68Drizzle melted chocolate over the pudding on each cookie.
  69. 69Drizzle melted chocolate over the pudding on each cookie.
  70. 70Top each cookie with sliced strawberries.
  71. 71Top each cookie with sliced strawberries.
  72. 72Top each cookie with sliced strawberries.

Ingredients

  • 1 cup whole milk
  • 1 cup whole milk
  • 1 cup whole milk
  • 1 box vanilla pudding
  • 1 box vanilla pudding
  • 1 box vanilla pudding
  • 2 tsp strawberry extract
  • 2 tsp strawberry extract
  • 2 tsp strawberry extract
  • 2 cups sliced frozen strawberries
  • 2 cups sliced frozen strawberries
  • 2 cups sliced frozen strawberries
  • 8 oz Cool Whip
  • 8 oz Cool Whip
  • 8 oz Cool Whip
  • 4.5 cups AP Flour
  • 4.5 cups AP Flour
  • 4.5 cups AP Flour
  • 1 cup cocoa powder
  • 1 cup cocoa powder
  • 1 cup cocoa powder
  • 1 tsp salt
  • 1 tsp salt
  • 1 tsp salt
  • 0.5 tsp baking soda
  • 0.5 tsp baking soda
  • 0.5 tsp baking soda
  • 0.5 tsp cream of tartar
  • 0.5 tsp cream of tartar
  • 0.5 tsp cream of tartar
  • 1 cup unsalted butter, softened
  • 1 cup unsalted butter, softened
  • 1 cup unsalted butter, softened
  • 1.33 cups granulated sugar
  • 1.33 cups granulated sugar
  • 1.33 cups granulated sugar
  • 0.75 cups powdered sugar
  • 0.75 cups powdered sugar
  • 0.75 cups powdered sugar
  • 0.75 cups vegetable oil
  • 0.75 cups vegetable oil
  • 0.75 cups vegetable oil
  • 2 large eggs, room temp
  • 2 large eggs, room temp
  • 2 large eggs, room temp
  • 1 tbsp water
  • 1 tbsp water
  • 1 tbsp water
  • strawberries
  • strawberries
  • strawberries
  • chocolate
  • chocolate
  • chocolate

Equipment

whiskbowlspatulabaking sheetparchment paperscoopcookie cutterknifecutting boardpiping bag

Tips

  • No chill time required for the cookie dough.
  • Make a pocket in the middle of the cookie dough balls before baking to hold the pudding.
  • Consider topping with a full chocolate-dipped strawberry for extra flair if feeling frisky