Ingredients
Pineapple Jam
- 20 ounce can pineapple slices or chunks packed in juice
- 8 ounce can pineapple slices or chunks packed in juice
- ¼ cup granulated sugar
Cookie Dough
- 1 ¼ cups all-purpose flour
- 1 tablespoon cornstarch
- ⅛ teaspoon salt
- 4 tablespoons powdered sugar
- ½ cup unsalted butter room temperature
- 1 egg yolk
- ½ teaspoon pineapple flavoring optional
Egg Wash Coating
- 1 egg yolk
- ½ tablespoon condensed milk regular milk can be substituted but will produce a less shiny coating
Instructions
Pineapple Jam
- Drain the canned pineapple, and then, using your hands squeeze out any additional juice.
- In a blender or food processor, puree the pineapple for 10 seconds.
- In a medium saucepan over medium-low heat, combine the pineapple puree and ¼ cup sugar. Mix continually with a wooden spoon until thickened (approximately 30 minutes). Set aside to cool.
Cookie Dough
- Preheat the oven to 325°. Line a baking sheet with parchment paper.
- In a large bowl, whisk together flour, cornstarch, salt, and confectioners sugar.
- In the bowl of a stand mixer (or in a food processor or by hand) combine the flour mixture, butter, 1 egg yolk, and (optional) pineapple flavoring until a smooth dough forms.
- To make cookies, first prepare balls of pineapple filling. Scoop ¼ heaping teaspoon of filling and roll into a ball. Roll 16 filling balls.
- Use a small scoop or 1 tablespoon, to scoop a ball of dough. Flatten the scoop of dough into a disc shape and place a filling ball in the center of the dough disc. Wrap the dough around the filling, and roll the dough into a ball.
- Place the filled dough balls on the prepared cookie sheet at least 2″ apart.
- Press the back of a butter knife into the top of the cookie dough ball to create a criss-cross pattern.
- Combine the egg yolk and condensed milk to make an egg wash.
- Brush the top of each cookie with the egg wash.
- Bake for 18-20 minutes or until the tops of the cookies are golden brown and the bottom edge begins to brown.
- Allow to cool on the baking pan for 5-10 minutes before transferring to a wire rack to cool completely.
- Store cooled cookies in an airtight container at room temperature for up to 1 week.

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