If you adore the nostalgic charm of classic pineapple upside-down cake but crave something a little more handheld and snackable, you are going to fall head over heels for this Pineapple Upside Down Cookies Recipe. Imagine soft sugar cookies crowned with a glossy pineapple ring and a bright maraschino cherry right in the center—each bite bursting with buttery sweetness and a hint of tangy fruitiness. These individual delights bring all the warmth and sunshine of the original dessert into perfectly portioned cookies that are as fun to make as they are to eat. Whether you’re baking for a party, a family gathering, or simply because you deserve a sweet treat, these cookies will quickly become a cherished favorite.

Ingredients You’ll Need

A metal tray holds ten white bowls and a stick of butter, all arranged neatly on a white marbled surface. At the top right, a large white bowl is filled with light beige flour, and next to it on the left is a smaller white bowl with a clear pale yellow liquid. Beside that is a tiny white bowl with amber syrup. Near the center is one white egg sitting directly on the tray. Below the egg, a small white bowl contains bright red cherries. To the left of the cherries, a clear glass bowl holds a white powder, possibly baking soda. Below this, a white bowl is filled with brown sugar, textured and slightly mounded. To the right of the brown sugar, at the bottom right of the tray, another white bowl displays four stacked pale yellow pineapple rings. Above the pineapple, a medium white bowl holds granulated white sugar. The butter stick, wrapped with a vintage label, lies horizontally near the center bottom of the tray. photo taken with an iphone --ar 4:5 --v 7

This Pineapple Upside Down Cookies Recipe comes together beautifully with ingredients that are simple yet essential. Each one plays a role in creating that perfect balance of sweet, soft, and fruity, ensuring you get the most delightful texture and irresistible flavor in every bite.

½ cup Butter, softened: Adds richness and moisture, helping the cookie dough come together smoothly.
½ cup Granulated Sugar (100g): Provides sweetness and helps achieve that lightly crisp edge on the cookies.
1 Large Egg: Acts as a binder, giving structure and tenderness to the dough.
1 teaspoon Vanilla Extract: Enhances flavor depth with its warm, aromatic notes.
½ cup Powdered Sugar (65g): Helps make the cookies extra soft and slightly more tender.
¼ cup Vegetable Oil: Keeps the cookies moist without weighing them down.
½ teaspoon Baking Soda: A leavening agent adding lift and lightness.
½ teaspoon Cream of Tartar: Works with baking soda for a perfect rise and smooth texture.
2 cups All-Purpose Flour (240g): The foundation of your cookies, balancing chewiness and sturdiness.
Pineapple Rings, drained: Offer that juicy, tropical sweetness and signature look for the topping.
Maraschino Cherries, drained: Adds a pop of vibrant color and a sweet cherry burst.
6 tablespoons Butter, melted: Blended with brown sugar to create the luscious caramelized topping.
1 cup Brown Sugar (214g): Infuses deep caramel flavor and creates that iconic golden crust under each cookie.

How to Make Pineapple Upside Down Cookies Recipe

Step 1: Prepare Your Pan and Pineapple Topping

Start by preheating your oven to 350 degrees Fahrenheit. This step ensures that your cookies bake evenly right from the get-go. Next, mix the melted butter with brown sugar in a small bowl until smooth—that sweet buttery mixture is going to form the caramelized base for each cookie’s topping. Drain your pineapple rings well to avoid soggy cookies. Then, spoon about one tablespoon of the brown sugar butter mixture into each muffin cup and press a pineapple ring on top, followed by a maraschino cherry nestled neatly in the center. A little tip: stagger how you place the cookies in the pan so they have space to spread without merging.

Step 2: Make the Cookie Dough

In a mixing bowl, cream together the softened butter and granulated sugar until the mixture becomes light and fluffy. Don’t rush here—taking your time will make the dough wonderfully tender. Beat in the egg and vanilla extract, continuing to mix for a few more minutes. Then gradually add the vegetable oil and powdered sugar—this combination gives the dough a silky smooth texture and a pale golden hue. Combine the all-purpose flour, baking soda, and cream of tartar in a separate bowl before incorporating the dry mixture gently into the wet ingredients until just combined. The dough should be soft but easy to handle.

Step 3: Shape and Bake

Use a cookie scoop (size #24 works perfectly) to portion the dough, then flatten each ball into a roughly 3-inch disk with your palm—it should be wide enough to cover the pineapple ring and cherry perfectly. Place the flattened dough over the prepared pineapple and cherry in each muffin cup, gently pressing the edges against the sides to secure the dough in place. Bake at 350 degrees for 8 to 10 minutes or until the edges turn just golden and the centers are no longer shiny. Once baked, carefully invert the muffin tin onto a parchment-lined cookie sheet—watch the magic happen as the cookies fall out, revealing their iconic upside-down fruit topping.

How to Serve Pineapple Upside Down Cookies Recipe

A woman's hand holds a small round cake showing three main layers: the base is a light golden yellow sponge cake with a soft texture, topped with a shiny caramel-colored layer, and finally a large bright yellow pineapple ring with visible fibrous texture sits on top, centered by a glossy red cherry. In the background, several similar cakes rest on a white metal cooling rack over a white marbled surface with a soft red cloth nearby. The lighting highlights the tropical, fresh look of the cakes. photo taken with an iphone --ar 4:5 --v 7

Garnishes

These cookies shine on their own, but you can elevate the presentation by dusting them lightly with powdered sugar or drizzling a bit of honey or caramel sauce for extra sweetness. For a refreshing contrast, a sprig of fresh mint adds a beautiful pop of green and a subtle herbal brightness.

Side Dishes

Serve these Pineapple Upside Down Cookies alongside a scoop of vanilla bean ice cream or a dollop of whipped cream to complement the fruity caramel flavors with creamy coolness—a truly indulgent pairing. Fresh fruit or a tropical fruit salad makes an also excellent accompaniment if you want to keep things light and vibrant.

Creative Ways to Present

Turn your cookies into a charming dessert platter by arranging them on a decorative serving tray and surrounding them with sliced pineapple wedges and cherries. For parties, consider skewering a cookie with a pineapple chunk and cherry on a cocktail stick to create playful handheld treats that guests will adore.

Make Ahead and Storage

Storing Leftovers

These cookies stay fresh when stored in an airtight container at room temperature for up to 3 days. Keeping them covered well preserves their softness and the luscious caramel topping.

Freezing

If you want to make a batch ahead of time, Pineapple Upside Down Cookies freeze wonderfully. Place them in a single layer on a baking sheet to freeze, then transfer to a freezer-safe container or bag. They’ll keep for up to 2 months without losing their flavor or texture.

Reheating

To bring frozen cookies back to life, allow them to thaw at room temperature for about 30 minutes, then warm briefly in a preheated 300-degree oven for 5 minutes. This refreshes the caramel topping and gives the cookies a just-baked glow.

FAQs

Can I use canned pineapple rings for this recipe?

Yes, canned pineapple rings work perfectly. Just make sure to drain them thoroughly to avoid sogginess that could affect the cookie texture.

What if I don’t have cream of tartar?

If cream of tartar isn’t on hand, you can substitute it with an equal amount of lemon juice or vinegar to activate the baking soda, though the texture may be slightly different.

Can these cookies be made gluten-free?

Absolutely! Swap the all-purpose flour for a gluten-free flour blend suitable for baking; just be sure your blend contains xanthan gum for structure.

How long do the cookies need to cool before flipping out of the pan?

Allow the cookies to cool in the pan for about 5 minutes—just enough to set slightly but still warm to easily release when flipped.

Can I make these cookies dairy-free?

Yes, you can use dairy-free butter substitutes and oil in place of butter to make these cookies dairy-free while maintaining that rich, tender crumb.

Final Thoughts

There is something undeniably joyful about these Pineapple Upside Down Cookies Recipe that brings sunshine to any day. The way the soft sugar cookie hugs the caramelized pineapple and cherry topping is pure comfort in a bite-sized form. I promise, once you try these, they’ll quickly become your go-to when you want a treat that’s both nostalgic and fresh. Go ahead and bake a batch—you won’t regret sharing this sweet treasure with friends and family!

Pineapple Upside Down Cookies Recipe

Ingredients You’ll Need

How to Make Pineapple Upside Down Cookies Recipe