Pineapple Thumbprints

  • Level: Easy
  • Yield: about 36 cookies
  • Total: 4 hr
  • Prep: 2 hr 45 min
  • Inactive: 1 hr
  • Cook: 15 min
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Ingredients

2 cups all-purpose flour

1/2 teaspoon baking powder

1/2 teaspoon salt

10 tablespoons unsalted butter, at room temperature

1/3 cup packed light brown sugar

1/3 cup plus 2 teaspoons granulated sugar

1 large egg

1 tablespoon fresh lemon juice

1/2 cup dried pineapple chunks, finely chopped, plus more for topping

1/3 cup canned crushed pineapple in juice

1 1/2 ounces cream cheese

1/4 teaspoon pure vanilla extract

1/4 teaspoon finely grated lemon zest

Milk, for brushing

Directions

  1. Whisk the flour, baking powder and salt in a medium bowl. Beat the butter, brown sugar and 1/3 cup granulated sugar in a large bowl with a mixer on medium speed until light and fluffy, about 3 minutes. Beat in the egg, then the lemon juice. Reduce the mixer speed to medium low; mix in the dried pineapple, then the flour mixture until combined. Cover and refrigerate until firm, about 30 minutes.
  2. Meanwhile, combine the crushed pineapple, cream cheese, the remaining 2 teaspoons granulated sugar, the vanilla and lemon zest in a bowl with a rubber spatula, breaking up any large pineapple pieces. Refrigerate until slightly firm, at least 30 minutes.
  3. Position racks in the upper and lower thirds of the oven; preheat to 350 degrees F. Line 2 baking sheets with parchment paper. Roll the dough into 1-inch balls; arrange 2 inches apart on the baking sheets. Indent each with the back of a floured 1/4 teaspoon measuring spoon; brush with milk.
  4. Bake, switching the pans halfway through, until the cookies are slightly puffed, 10 to12 minutes. Remove from the oven andre-indent; spoon in the filling. Return to the oven until lightly browned, 6 to 8 more minutes. Let cool 5 minutes on the baking sheets; transfer to racks to cool completely. Top with dried pineapple.

Let's Get Cooking!

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Amanda B.

Love these cookies! This is the second year making them and they turned out very yummy. Don't be deterred by the how long these take, it's mostly chill time. I make the dough ahead of time and leave it in the fridge over night then make the rest the next day. Pro tip: if leaving over night take the dough out 30 mins before using or else the dough will crack when pressing in the teaspoon. The milk makes a nice little crust on the outside so dont skip that part!! Highly recommend. 

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