I have a confession to make. I absolutely adore the classic pineapple upside-down cake, but I rarely have the patience to actually make one.
It’s that whole cake-flipping spectacle. The anxiety of it sticking to the pan, the mess, the commitment to a full-sized cake… sometimes it’s just too much.
That’s when this idea hit me. What if I could capture all that caramelized, fruity goodness in a simple, single-serving cookie? No flipping required.
After a few wonderfully tasty experiments, this recipe was born. It combines a soft, buttery sugar cookie base with that iconic pineapple and cherry topping. It’s a little bite of sunshine.
What You’ll Need
Here’s everything you’ll need to gather before you get started. I’ve broken it down into the topping and the cookie dough to keep things simple.
For the Topping
- 1/2 cup unsalted butter, melted
- 1 cup packed light brown sugar
- 1 (20 ounce) can pineapple rings in juice, drained
- 12-15 maraschino cherries, stems removed
For the Sugar Cookies
- 2 1/2 cups all-purpose flour
- 1 teaspoon baking soda
- 1/2 teaspoon salt
- 1 cup unsalted butter, softened to room temperature
- 3/4 cup granulated sugar
- 1 large egg
- 1 teaspoon vanilla extract
Tools Required
You don’t need any fancy equipment for this recipe. Here are the basics that will get the job done.
- Standard 12-cup muffin tin
- Mixing bowls (one large, one medium)
- Electric mixer (handheld or stand mixer)
- Whisk
- Spatula
- Measuring cups and spoons
- Paper towels
How to Make Pineapple Upside Down Sugar Cookies
Follow these simple steps for perfect cookies every time. Don’t rush the process, especially the chilling step!
Part 1: Prepare the Topping
Step 1: Preheat your oven to 375°F (190°C). Don’t grease your muffin tin; the butter in the topping will take care of that.
Step 2: In a small bowl, mix the melted butter and brown sugar until they are well combined. The mixture should look like wet sand.
Step 3: Evenly distribute the brown sugar mixture among the 12 cups of your muffin tin. This is about 1 tablespoon per cup.
Step 4: Take your drained pineapple rings and pat them thoroughly dry with paper towels. This is a crucial step to prevent the cookies from getting soggy.
Step 5: Place one pineapple ring into each muffin cup, pressing it gently into the brown sugar mixture. Place a maraschino cherry in the center of each pineapple ring.
Part 2: Make the Cookie Dough
Step 6: In a medium bowl, whisk together the all-purpose flour, baking soda, and salt. Set this dry mixture aside for later.
Step 7: In a large bowl using an electric mixer, beat the softened butter and granulated sugar on medium-high speed until the mixture is light and fluffy. This usually takes about 2-3 minutes.
Step 8: Beat in the large egg and vanilla extract until they are just combined. Make sure to scrape down the sides of the bowl with a spatula to incorporate everything.
Step 9: With the mixer on low speed, gradually add the dry flour mixture to the wet ingredients. Mix until just combined. Be careful not to overmix the dough.
Part 3: Assemble and Bake
Step 10: The dough will be soft. Scoop out portions of the dough (about 2 tablespoons each) and gently place them on top of the pineapple and cherry in each muffin cup.
Step 11: There’s no need to press the dough down hard. It will melt and spread over the topping as it bakes.
Step 12: Bake for 12-15 minutes, or until the edges of the cookies are golden brown. The center might still look a little soft.
Step 13: Remove the muffin tin from the oven and let it cool on a wire rack for exactly 5 minutes. This is the sweet spot; too soon and they fall apart, too long and the caramel will harden in the pan.
Step 14: Carefully run a thin knife or spatula around the edge of each cookie. Place a baking sheet or cutting board over the muffin tin and, using oven mitts, carefully flip it over. Lift the muffin tin away. If any topping sticks, just scoop it out and place it back on the cookie.
Step 15: Let the cookies cool completely on the baking sheet before enjoying.
Pro Tips
I’ve made these cookies more times than I can count. Here are a few hard-won tips that will make your first batch a huge success.
- Pat That Pineapple Dry. Seriously. I know I mentioned it before, but it’s the most important tip. Excess juice will turn your cookie bottoms into a mushy mess. Squeeze them gently and pat them with paper towels until they feel dry to the touch.
- Don’t Skip the 5-Minute Cool Down. The timing for the flip is critical. The 5-minute window allows the caramel to set just enough so it’s not pure liquid, but not so much that it glues the cookies to the pan. Set a timer!
- Softened Butter is Key. Make sure your butter for the cookie dough is properly softened to room temperature, not melted. Properly creamed butter and sugar create air pockets that give the cookies a soft, tender texture.
- Avoid Overmixing the Dough. Once you add the flour, mix only until you no longer see white streaks. Overmixing develops the gluten in the flour, which can lead to tough, dense cookies instead of soft, chewy ones.
Substitutions and Variations
This recipe is great as is, but you can easily tweak it to fit your tastes or what you have in your pantry.
| Ingredient | Substitution/Variation | Notes |
|---|---|---|
| Pineapple Rings | Crushed Pineapple | Drain and press very well. |
| Maraschino Cherry | Pecan Halves | Adds a nice crunch. |
| Light Brown Sugar | Dark Brown Sugar | Creates a richer, molasses flavor. |
| Vanilla Extract | Rum or Coconut Extract | Use half the amount for a tropical twist. |
Nutrition, Diets, and Pairings
Here’s a quick look at the nutritional side of things and how to adapt the recipe for different dietary needs.
Approximate Nutritional Information
This is an estimate per cookie, based on the recipe making 12 cookies. Actual values may vary.
| Nutrient | Amount per Cookie |
|---|---|
| Calories | ~350 kcal |
| Fat | ~18g |
| Carbohydrates | ~45g |
| Protein | ~3g |
Ingredient Swaps for Dietary Needs
- Gluten-Free: Swap the all-purpose flour with a high-quality 1-to-1 gluten-free baking flour blend that contains xanthan gum.
- Dairy-Free: Use a good quality plant-based butter substitute in both the topping and the cookie dough. Ensure it’s the kind that comes in sticks, not a soft tub spread.
Pairing Suggestions
These cookies are a treat all on their own, but they pair wonderfully with a simple cup of black coffee or a strong black tea to cut through the sweetness.
For a more decadent dessert, serve a warm cookie alongside a scoop of vanilla bean or coconut ice cream.
Leftovers and Storage
If you happen to have any cookies left over, here’s the best way to store them.
Store the cookies in a single layer in an airtight container. You can keep them at room temperature for up to 3 days.
Placing a sheet of wax paper or parchment paper between layers can prevent them from sticking together if you need to stack them.
I don’t recommend freezing the baked cookies, as the pineapple topping can become watery upon thawing. However, you can freeze the cookie dough for up to 3 months.
Frequently Asked Questions
Q1. My caramel topping was too hard and stuck to the pan. What happened?
Ans: This usually means the cookies were left to cool in the pan for too long before flipping. The brown sugar mixture will harden as it cools. Try to stick to that 5-minute window for the perfect flip.
Q2. Why did my cookies turn out soggy on the bottom?
Ans: The most likely culprit is wet pineapple. You have to be very thorough about patting the pineapple rings dry. Any excess juice will seep into the cookie dough during baking.
Q3. Can I make this recipe in a different pan?
Ans: A standard muffin tin works best because it contains the caramel and gives the cookies their signature shape. Using a flat baking sheet would result in the caramel and butter spreading everywhere.
Q4. My cookie dough was very sticky and hard to handle. Is that normal?
Ans: Yes, this is a soft dough. If it’s too difficult to scoop, you can chill the dough for about 30 minutes before portioning it into the muffin tin. This will make it firmer and easier to work with.
Wrapping Up
There you have it all the joy of a pineapple upside-down cake packed into one perfect, easy-to-make cookie. It’s a truly delightful treat that’s perfect for sharing (or not!).
I really hope you give this recipe a try. It’s become a favorite in my house, and I think it will in yours, too.
If you do make them, please leave a comment below! I love hearing about your experiences and answering any questions you might have.
