These Pineapple Upside Down Delight Cookies take all the flavors of the classic cake and transform them into soft, buttery cookies topped with sweet pineapple slices. With a hint of vanilla and the richness of sour cream, these cookies are perfectly moist, slightly tangy, and irresistibly delicious.

Why You’ll Love This Recipe

Inspired by a classic dessert – a fun twist on pineapple upside-down cake
Soft and chewy – thanks to sour cream for extra moisture
Easy to make – with simple ingredients and a straightforward method
Perfect balance of flavors – sweet pineapple with a buttery vanilla cookie base
Great for any occasion – from summer picnics to holiday baking

Ingredients

(Tip: You can find the complete list of ingredients and their measurements in the recipe card below.)

1 cup butter (room temperature)
1½ cups granulated sugar
2 eggs
2 teaspoons vanilla extract
½ cup sour cream
3 cups all-purpose flour
1 teaspoon baking powder
1 teaspoon cornstarch
½ teaspoon salt
13 canned pineapple slices (drained and patted dry)

Directions

1. Prepare the Cookie Dough

Preheat oven to 350°F (175°C). Line a baking sheet with parchment paper.
In a large bowl, cream butter and sugar until light and fluffy.
Add eggs, vanilla extract, and sour cream, mixing until well combined.

2. Mix Dry Ingredients

In a separate bowl, whisk together flour, baking powder, cornstarch, and salt.
Gradually add the dry ingredients to the wet mixture, mixing until just combined.

3. Shape and Add Pineapple

Scoop tablespoon-sized portions of dough onto the prepared baking sheet.
Flatten slightly and gently press a pineapple slice on top of each cookie.

4. Bake

Bake for 12-15 minutes, or until the edges are golden brown.
Let cool on the baking sheet for 5 minutes, then transfer to a wire rack to cool completely.

Servings and Timing

Servings: 13 large cookies
Prep Time: 15 minutes
Bake Time: 12-15 minutes
Total Time: 30 minutes

Variations

Cherry on Top: Place a maraschino cherry in the center of each pineapple slice before baking.
Caramelized Flavor: Sprinkle brown sugar on top for a caramelized effect.
Coconut Twist: Add ½ cup shredded coconut to the dough for a tropical touch.
Nutty Crunch: Mix in ¼ cup chopped pecans for extra texture.

Storage

Room Temperature: Store in an airtight container for up to 3 days.
Refrigeration: Keep in the fridge for up to 5 days for longer freshness.
Freezing: Freeze baked cookies for up to 2 months. Thaw at room temperature before serving.

FAQs

1. Can I use fresh pineapple instead of canned?

Yes! Just slice it thinly and pat dry to remove excess moisture.

2. How do I keep my cookies soft?

Do not overbake, and store in an airtight container with a slice of bread to retain moisture.

3. Can I make these cookies smaller?

Yes! Use smaller dough portions and cut the pineapple into smaller pieces.

4. What’s the best way to drain pineapple slices?

Place them on paper towels and gently press to remove excess juice.

5. Can I use Greek yogurt instead of sour cream?

Yes! Greek yogurt is a great substitute for sour cream.

6. How do I prevent the pineapple from making the cookies soggy?

Make sure the pineapple slices are fully drained and dried before pressing them onto the dough.

7. Can I add a drizzle of glaze?

Yes! A simple powdered sugar and milk glaze would be a delicious finishing touch.

8. Can I use a cookie cutter to shape the dough?

You can roll out the dough and cut it into shapes for a more uniform look.

9. Can I make the dough ahead of time?

Yes! Refrigerate the dough for up to 24 hours before baking.

10. What pairs well with these cookies?

Enjoy with vanilla ice cream, whipped cream, or a cup of tea for a delightful treat!

Conclusion

These Pineapple Upside Down Delight Cookies bring the nostalgic flavors of a classic cake into a fun, handheld dessert. With a buttery cookie base and juicy pineapple topping, every bite is packed with tropical sweetness. Try them today and enjoy a unique, crowd-pleasing treat!