Upside-Down Pineapple Cake Cookies: A Cookie That Flips the Script

What happens when you take one of the most iconic retro desserts—the pineapple upside-down cake—and smash it into cookie form?
You get buttery edges, tropical flavor bombs, and a cookie that quite literally turns dessert traditions on their head.

Inspired by the Bake It Fat & Weird crew’s latest creation, this cookie is part nostalgia, part innovation, and 100% sunshine in snack form. Whether you’re baking for a BBQ, a summer party, or just to flex your skills in the kitchen, these Upside-Down Pineapple Cake Cookies bring serious "main character" energy.

Let’s Talk Flavor:

Think brown sugar caramelized pineapple, creamy white chocolate, and juicy maraschino cherries all packed into a thick, golden-brown cookie. Now picture a surprise cake core bursting in the center. That’s right—this cookie isn’t just inspired by cake... it is cake (stuffed inside a cookie).

It’s tropical, gooey, chewy, and crunchy in all the right ways.

The Recipe: Upside-Down Pineapple Cake Cookies

Time to flip tradition on its head—one cookie at a time!

Ingredients (All in grams):

Butter: 113g
Shortening: 113g
Sugar: 216g
Brown Sugar: 126g
Flour: 575g
Baking Powder: 8g
Cornstarch: 10g
Salt: 3g
Eggs: 105g
Pineapple Emulsion: 7g
Vegetable Oil: 10g

Mix-Ins / Filling / Topping:

White Chocolate Chips
Pineapple Chunks
Pineapple Rings
Maraschino Cherries

Optional Cake Core:

Mix pre-baked cake (store-bought or leftover) with pineapple and cherry juice. Freeze into small portions to stuff inside the cookies.

Directions:

Optional Prep:

Mix crumbled cake with pineapple and cherry juice.
Freeze into small stuffed cores.

1. Cream the Fats & Sugars:

In a large bowl, cream together butter, shortening, sugar, and brown sugar until light and fluffy.

2. Add Wet Ingredients:

Beat in the eggs, pineapple emulsion, and vegetable oil until fully incorporated.

3. Add Dry Ingredients:

Mix in baking powder, cornstarch, and salt.

4. Add Flour:

Gradually incorporate flour until a soft dough forms.

5. Fold in Mix-Ins:

Gently fold in white chocolate chips and pineapple chunks.

6. Portion:

Divide dough into 5 oz balls for even baking.

7. Optional Cake Core:

Form dough into cups and stuff with frozen cake mixture for an ultra-cakey center.

8. Chill the Dough:

Refrigerate or freeze the dough balls for 1–2 hours to prevent spreading and boost flavor.

9. Bake:

Preheat oven to 375°F (190°C).
Line a baking sheet and sprinkle a small amount of brown sugar where each cookie will sit.
Place a pineapple ring on top of the sugar, then pre-bake for 15 minutes.
Add a cherry to the ring center, then top with a dough ball.
Bake for 22–24 minutes until golden and set. Adjust time for size.

10. Cool & Garnish:

Let cookies cool for 10 minutes.
Drizzle with melted white chocolate and top with an extra cherry if you’re feeling fancy.

A Cookie That Tastes Like Vacation

These Upside-Down Pineapple Cake Cookies are the best of both worlds: the chewy indulgence of a bakery-style cookie, and the fruity caramelized magic of a classic pineapple cake. Sweet, a little nostalgic, and very weird—in the best way.

Bake it. Flip it. Love it.

Baking Essentials

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