If you love the nostalgic charm of classic pineapple upside-down cake but are craving a handheld treat that’s perfect for sharing, you are going to absolutely adore this Pineapple Upside-Down Cookies Recipe. These delightful cookies capture all the tropical sweetness and buttery richness of the original dessert but in a perfectly sized, portable cookie form. Each bite offers a wonderful contrast between the caramelized pineapple and cherry topping and the soft, flavorful sugar cookie beneath. It’s a uniquely fun and delicious way to enjoy a timeless favorite, and I can’t wait to walk you through every delicious detail!
Ingredients You’ll Need
Gathering your ingredients is the first joyful step toward baking these irresistible treats. Each one plays a crucial role, creating a balance of sweet, tangy, and tender textures that make the Pineapple Upside-Down Cookies Recipe stand out.
- Pineapple slices: Using canned pineapple in juice ensures consistent sweetness and moisture, making each cookie perfectly juicy.
- Maraschino cherries: These add a bright pop of color and a hint of sweet tartness, perfectly complementing the pineapple.
- Betty Crocker™ Sugar Cookie Mix: This mix forms the buttery, soft base cookie with just the right hint of sweetness and crumb.
- Vanilla instant pudding and pie filling mix (dry): Adding this dry mix enhances the cookie’s texture, making it extra tender and rich.
- Butter (softened): Butter enriches the dough, contributing to flavor and that melt-in-your-mouth softness you want in each cookie.
- Brown sugar: Packed with molasses, this sugar adds depth and a gentle caramel note to the dough.
- Vanilla extract: A splash of vanilla elevates all the flavors, bringing warmth and richness to the cookie dough.
- Egg: Eggs bind the ingredients together, giving structure and tenderness to your cookies.
How to Make Pineapple Upside-Down Cookies Recipe
Step 1: Prepare Your Oven and Cookie Sheets
Preheat your oven to 350°F to ensure even baking from the start. Line two large cookie sheets with parchment paper, which will prevent sticking and help you lift the cookies easily after baking. This step may seem simple, but a well-prepped baking surface makes all the difference for perfectly shaped cookies.
Step 2: Drain Pineapple and Save the Juice
Drain the pineapple slices carefully on a paper towel-lined tray to remove excess moisture while keeping the juice to add into your cookie dough. This reserved pineapple juice infuses the dough with extra tropical flavor, so don’t toss it out! It’s a clever little trick that really elevates the recipe.
Step 3: Arrange Pineapple and Cherries on Sheets
Place seven pineapple rings evenly spaced on each cookie sheet. Nestle a maraschino cherry into the center of each pineapple ring. This step creates the iconic “upside-down” look and sets the stage for that beautiful caramelized topping effect once baked.
Step 4: Mix Cookie Dough
In a large bowl, combine the sugar cookie mix, vanilla pudding mix, softened butter, brown sugar, the reserved pineapple juice, vanilla extract, and egg. Stir everything together with a spoon until you get a soft, cohesive dough. The pudding mix is the secret weapon here, adding moisture and a tender crumb without weighing down the dough.
Step 5: Shape Dough Over Pineapple Rings
Divide the dough into fourteen balls, roughly 3 tablespoons each, and place one ball directly over each pineapple ring and cherry. Gently flatten the dough slightly—this helps it spread evenly during baking and trap in all those luscious fruit flavors.
Step 6: Bake and Cool
Bake the cookies for 22 to 27 minutes, watching for golden brown edges and a slightly cracked top. Once baked, cool the cookies on the pan for 10 minutes, then carefully flip them upside down onto a cooling rack to fully reveal their beautiful pineapple and cherry “tops.” Allow to cool completely before serving for the best texture and presentation.
How to Serve Pineapple Upside-Down Cookies Recipe
Garnishes
For an extra touch of sparkle and flavor, consider dusting your cooled cookies lightly with powdered sugar or a drizzle of coconut glaze. A small fresh mint leaf on top adds a wonderful fresh contrast and makes each cookie feel like a tiny tropical celebration.
Side Dishes
These cookies shine on their own but can be paired beautifully with a scoop of vanilla ice cream or a dollop of whipped cream for an indulgent dessert twist. Serving alongside a cup of freshly brewed coffee or tropical fruit iced tea also enhances the bright fruit flavors wonderfully.
Creative Ways to Present
Try arranging these cookies on a wooden serving platter lined with banana leaves for a fun, island-inspired vibe. Alternatively, present them stacked in a decorative jar or gift box to share the joy with friends and family. Their vibrant colors and iconic look make them a guaranteed hit at parties and gatherings.
Make Ahead and Storage
Storing Leftovers
Place any leftover cookies in a single layer inside an airtight container, loosely covered to prevent condensation. They will stay soft and flavorful for up to one day, though they rarely last that long because they are so irresistible!
Freezing
For longer storage, freeze the cookies in an airtight container or freezer bag with parchment paper between layers to prevent sticking. They freeze well for up to one month and thaw quickly at room temperature when you’re ready to enjoy.
Reheating
Reheat cookies briefly in a preheated 300°F oven for about 5 minutes to warm them through and refresh their soft, gooey texture. Avoid microwaving, which can make the cookies overly soft or chewy instead of tender and perfect.
FAQs
Can I use fresh pineapple instead of canned for the Pineapple Upside-Down Cookies Recipe?
Fresh pineapple can be used, but canned pineapple in juice ensures consistent sweetness and moisture levels, making the cookie texture more predictable and reliable.
What if I don’t have vanilla pudding mix?
You can substitute with instant vanilla pudding mix or add a teaspoon of cornstarch to the dough for similar texture enhancement, though the official pudding mix really adds that tender softness.
Can I make these cookies gluten-free?
Using a gluten-free sugar cookie mix instead of the Betty Crocker™ mix will work, but make sure that all other ingredients are certified gluten-free to avoid cross-contamination.
Why do I need to flip the cookies after baking?
Flipping reveals the caramelized pineapple and cherry “upsides” that are the signature of this recipe, mimicking the classic upside-down cake appearance and texture.
How do I prevent the cookie dough from sliding off the pineapple rings?
Slightly flattening the cookie dough balls over the pineapple rings helps them stick better and bake evenly without sliding around.
Final Thoughts
This Pineapple Upside-Down Cookies Recipe is a total crowd-pleaser that brilliantly reimagines a classic dessert into a fun, shareable cookie. Whether you’re baking for a special occasion or just to satisfy that tropical craving, these cookies deliver moist, fruity, buttery goodness in every bite. Give them a try and watch how quickly they become a new family favorite—you’ll want to bake these over and over!
Print
Pineapple Upside-Down Cookies Recipe
- Prep Time: 15 minutes
- Cook Time: 25 minutes
- Total Time: 2 hours 40 minutes
- Yield: 14 servings
- Category: Dessert
- Method: Baking
- Cuisine: American
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
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.
