Description
Delight in these Pineapple Upside-Down Cookies, featuring juicy pineapple rings and maraschino cherries baked under soft, flavorful sugar cookie dough enriched with vanilla pudding mix. This twist on the classic pineapple upside-down cake brings tropical sweetness and a chewy, tender texture in bite-sized form.
Ingredients
Scale
Fruit Topping
- 1 can (20 oz) pineapple slices in juice
- 1 can (8 oz) pineapple slices in juice
- 14 maraschino cherries, drained
Cookie Dough
- 1 pouch (17.5 oz) Betty Crocker™ Sugar Cookie Mix
- 1 box (4-serving size) vanilla instant pudding and pie filling mix (dry)
- 1/2 cup butter, softened
- 1/3 cup packed brown sugar
- 1 teaspoon vanilla extract
- 1 egg
- Reserved 2 tablespoons pineapple juice from drained cans
Instructions
- Prepare Oven and Baking Sheets: Preheat your oven to 350°F (175°C). Line two large cookie sheets with cooking parchment paper to prevent sticking and for easy cleanup.
- Drain Pineapple: Carefully drain the pineapple slices on a paper towel-lined tray to remove excess juice. Reserve 2 tablespoons of this juice for the cookie dough mixture. Save remaining juice for another use or discard.
- Arrange Pineapple and Cherries: Place 7 pineapple rings evenly spaced on each prepared cookie sheet. Place a maraschino cherry in the center of each pineapple ring, creating the classic upside-down motif.
- Mix Cookie Dough: In a large bowl, combine the sugar cookie mix, dry vanilla pudding mix, softened butter, brown sugar, reserved pineapple juice, vanilla extract, and egg. Mix with a spoon until a soft dough forms, ensuring all ingredients are well incorporated.
- Shape Cookies: Divide the dough into 14 balls, each about 3 tablespoons in size, approximately 2 inches in diameter. Place each ball directly over a pineapple ring on the cookie sheets. Flatten each ball slightly to spread dough evenly over the fruit.
- Bake Cookies: Bake in the preheated oven for 22 to 27 minutes or until the cookies turn golden brown and the tops show cracks, indicating doneness.
- Cool and Invert Cookies: Allow the cookies to cool on the cookie sheets for 10 minutes. Then, carefully remove the cookies and turn them upside down onto a cooling rack to cool completely, roughly 30 minutes. This step reveals the pineapple and cherry topping on the cookie surface.
- Store Cookies: Once completely cooled, store the cookies in a single layer, loosely covered, for up to 1 day to maintain freshness.
Notes
- Use parchment paper for easy cookie removal and to prevent sticking.
- Ensure the pineapple slices are well drained to avoid soggy cookies.
- Do not skip flipping the cookies after baking, as this step presents the pineapple and cherry topping beautifully.
- Cookies are best enjoyed the same day but can be stored loosely covered for 1 day.
- Vanilla pudding mix adds moisture and a tender crumb to the cookies.
