Unsalted Butter: This foundational ingredient is key to creating the rich, golden caramel topping that defines this cake. Using unsalted butter allows you to control the overall salt content, ensuring a balanced sweetness without any unexpected savory notes. It also contributes to the tender crumb of the cake itself.

Brown Sugar (Packed): Packed brown sugar is indispensable for achieving that deep, luscious caramel layer. Its molasses content gives it a distinctive flavor and helps it melt into a glossy, sticky sauce that perfectly coats the pineapple slices, creating an irresistible sweet crust.

Pineapple Slices (Drained): The undeniable star of the topping, pineapple slices offer a delightful balance of sweet and tangy flavors. Using canned, drained slices is convenient and ensures uniform pieces that caramelize beautifully. Their natural acidity cuts through the sweetness, making each bite refreshing.

Maraschino Cherries: These vibrant cherries are not just for a pop of color; they add a burst of sweet, slightly almond-like flavor to the topping. Strategically placed, they create a beautiful visual appeal that makes the cake even more inviting.

All-Purpose Flour: As the primary structural component of the cake, all-purpose flour provides the necessary framework for a tender yet sturdy crumb. Sifting your flour can help ensure a lighter, airier texture.

Granulated Sugar: This fine white sugar sweetens the cake batter, contributing to its overall moistness and delicate texture. It balances the tang of the pineapple juice and works in harmony with the brown sugar in the topping.

Baking Powder: A crucial leavening agent, baking powder is responsible for the cake’s light and fluffy rise. It reacts when mixed with wet ingredients and again with heat, creating those wonderful airy pockets that give the cake its desirable texture.

Salt: A small amount of salt is a secret weapon in baking. It doesn’t make the cake taste salty, but rather enhances and balances all the other flavors, making the sweetness more pronounced and the pineapple brighter.

Milk: Milk adds essential moisture to the cake batter, contributing to its tenderness and richness. Whole milk is generally recommended for its fat content, which yields a more luxurious texture, but any milk will work.

Pineapple Juice: Beyond just adding moisture, pineapple juice infuses the cake batter with an additional layer of fruity flavor, reinforcing the tropical theme of the dessert. It also contributes to the cake’s tender crumb and moistness.

Vanilla Extract: Vanilla extract is a quintessential baking ingredient that provides a warm, aromatic, and comforting background flavor. It rounds out the sweetness and complements the fruit without overpowering it.

Large Eggs: Eggs play multiple roles in cake baking: they provide structure, act as a binder for the ingredients, and contribute to the cake’s richness and moisture. Using large eggs ensures consistent results for this recipe.

Achieving a picture-perfect pineapple upside down cake requires a few simple techniques. When arranging the pineapple slices and maraschino cherries in the skillet, don’t just place them – gently press them into the warm, gooey brown sugar mixture. This small but crucial step ensures they adhere well to the bottom of the pan, preventing them from floating or shifting when you pour the batter over the top. The result will be a more uniform, visually stunning, and structurally sound cake when you invert it. Another helpful tip is to ensure your skillet is adequately greased around the sides, even above the caramel layer, to prevent the cake from sticking during the inversion process. A non-stick skillet is ideal, but a well-seasoned cast iron skillet also works wonders for creating that beautiful caramelized crust. Don’t rush the cooling process; allowing the cake to cool for the recommended 10 minutes in the skillet before inverting is vital for the caramel to set slightly, ensuring it transfers cleanly to your serving plate without making a mess.

• Melted Unsalted Butter – Substitute with Melted Coconut Oil: Coconut oil offers a dairy-free alternative with a similar fat content and moisture, lending a subtle tropical aroma and flavor that naturally complements the pineapple. Ensure it’s fully melted before combining with sugar.

• Packed Brown Sugar – Substitute with Coconut Sugar: Coconut sugar provides a caramel-like sweetness reminiscent of brown sugar, making it an excellent natural alternative. It can be packed similarly and will contribute to a rich, less refined caramel topping.

• Drained Pineapple Slices – Substitute with Fresh Pineapple Slices: For an even brighter and crisper flavor, fresh pineapple can be sliced into rings and used in place of canned. Be sure to core each slice carefully for the best presentation and texture.

• Maraschino Cherries – Substitute with Fresh or Frozen Cherries: Opting for fresh or defrosted frozen cherries (pitted) provides a more natural tartness and intense fruit flavor, without the added preservatives or artificial dyes sometimes found in maraschino cherries. You could also use fresh raspberries or blueberries for a different fruit profile.

• All-Purpose Flour – Substitute with Whole Wheat Flour: For a slightly healthier twist and added fiber, whole wheat flour can be used. Note that it may result in a slightly denser cake with a nuttier flavor, so consider using a 50/50 blend with all-purpose flour for a softer crumb.

• Granulated Sugar – Substitute with Honey: Honey introduces natural sweetness and extra moisture to the cake. Because honey is sweeter than sugar, you might use slightly less (about ¾ cup honey for 1 cup sugar) and reduce other liquid ingredients slightly to maintain batter consistency.

• Baking Powder – Substitute with Baking Soda and Cream of Tartar: If you’re out of baking powder, you can create a homemade version. Use ¼ teaspoon of baking soda combined with ½ teaspoon of cream of tartar for every teaspoon of baking powder required. This combination provides the necessary leavening power.

• Salt – Substitute with Sea Salt: Fine sea salt can be used in the same quantity as regular table salt, offering a purer mineral flavor that enhances the overall taste profile of the cake effectively.

• Milk – Substitute with Almond Milk: For a dairy-free alternative, unsweetened almond milk works wonderfully, providing a similar consistency and contributing to a moist cake without altering the flavor profile significantly.

• Pineapple Juice – Substitute with Orange Juice: Orange juice makes for an excellent substitute, offering comparable acidity and sweetness. Its citrusy notes complement the tropical fruit flavors beautifully, adding a different but equally delicious dimension.

• Vanilla Extract – Substitute with Almond Extract: Almond extract delivers a distinct, nutty flavor that pairs exceptionally well with cherries and provides a sophisticated twist to the overall taste of the cake. Start with half the amount of almond extract as vanilla, as it is more potent.

• Large Eggs – Substitute with Flax Eggs: For a vegan option, create flax eggs by mixing 1 tablespoon of ground flaxseed with 3 tablespoons of water for each egg needed. Let the mixture sit for about 5 minutes until it thickens into a gel-like consistency, which effectively binds the cake ingredients.

• To maintain its exquisite texture and prevent any sogginess from condensation, always allow your freshly baked skillet pineapple upside down cake to cool completely on a wire rack before attempting any storage.
• Once cooled, carefully wrap the entire cake (or individual slices) tightly in plastic wrap, followed by a layer of aluminum foil. Ensure it is meticulously sealed to prevent air and moisture from compromising its freshness.
• For short-term enjoyment, place the well-wrapped cake in an airtight container and store it at room temperature. Under these conditions, it will remain deliciously fresh and moist for up to 2 days, ready for an impromptu treat.
• If you need to extend its shelf life, refrigerate the cake. Stored in the refrigerator, again tightly wrapped, your cake can be kept for up to 5 days. For the best flavor and texture, allow refrigerated slices to come to room temperature before serving.
• To freeze your delightful pineapple upside down cake, first wrap it thoroughly in plastic wrap, then enclose it in a second layer of aluminum foil. This double wrapping technique is crucial for providing an extra barrier against freezer burn and preserving its quality.
• Place the double-wrapped cake into a freezer-safe bag or an airtight container. Don’t forget to clearly label it with the date of freezing so you can easily keep track of its storage duration.
• The cake can be confidently frozen for up to 3 months. When you’re ready to indulge, simply transfer it to the refrigerator and allow it to thaw slowly overnight, ensuring it retains its moisture.
• For optimal warmth and texture revival, reheat the thawed cake. A preheated oven at 350°F (175°C) for approximately 10-15 minutes works wonders, bringing it back to its original comforting state.
• Alternatively, individual slices can be quickly reheated in the microwave. Heat on medium power for 20-30 seconds, checking frequently to prevent overcooking, which can lead to a dry or rubbery texture.
• Savor your skillet pineapple upside down cake, whether it’s fresh from the oven or perfectly preserved for later enjoyment!

• Oven Method: This is often the preferred method for reheating, as it best preserves the cake’s original texture. Preheat your oven to a gentle 300°F (150°C). Place any leftover slices of the Skillet Pineapple Upside Down Cake on a baking sheet. To prevent drying out, cover them loosely with aluminum foil. Heat for about 10-15 minutes, or until the cake is warmed through to the center. This method helps maintain the cake’s wonderful moist crumb and keeps the caramelized pineapple slices soft and gooey.

• Microwave Method: For a quick and convenient reheat, the microwave is your friend for individual slices. Place a single slice of cake on a microwave-safe plate. Cover it with a microwave-safe lid or a damp paper towel to trap steam and keep moisture in. Heat on medium power for 20-30 seconds initially. Check its warmth and add more time in short 10-second increments if necessary. Be extremely cautious not to overheat, as this can quickly turn the edges of the cake rubbery and compromise its delicate texture.

• Skillet Method: If you’re looking to refresh the caramelized topping and bring back a slight crispness to the edges, reheating in a skillet can be quite effective. Place the cake slices directly into a clean skillet over very low heat. Cover the skillet with a lid to trap heat and moisture. Heat for about 5-7 minutes, checking occasionally to ensure it doesn’t burn on the bottom. This method helps to re-crisp the bottom edges and enhances that rich buttery brown sugar flavor.

• Steam Method: For the gentlest reheating that ensures maximum moisture, consider using a steamer. Place the cake slices on a heatproof plate and set this plate into a steamer basket over simmering water (ensure the water doesn’t touch the plate). Steam for approximately 5 minutes. This technique is excellent for keeping the cake exceptionally moist and preventing any risk of it drying out, resulting in a wonderfully tender reheat.

• Air Fryer Method: An air fryer can provide a good balance between a slightly crisp exterior and a moist interior. Preheat your air fryer to 300°F (150°C). Place a slice of the cake directly into the air fryer basket. Heat for 3-5 minutes, carefully checking halfway through. This method can give a lovely slight crisp to the cake’s edges while keeping the interior perfectly moist and warm.

• Oven: A reliable oven is absolutely essential for baking the cake evenly and consistently at the specified temperature of 350°F (175°C), ensuring a perfectly cooked interior and golden-brown crust.

• 10-inch Skillet: This is the star tool for this recipe! A sturdy 10-inch skillet (preferably cast iron or oven-safe non-stick) is crucial for not only melting the butter and dissolving the brown sugar for the caramelized topping but also for beautifully arranging the pineapple slices and cherries, and finally, baking the cake itself.

• Mixing Bowl (for dry ingredients): You’ll need a medium-sized mixing bowl to thoroughly whisk together the dry ingredients such as all-purpose flour, granulated sugar, baking powder, and salt. This ensures they are well combined before liquids are added.

• Another Mixing Bowl (for wet ingredients): A separate mixing bowl is necessary for combining all the wet ingredients – milk, pineapple juice, vanilla extract, and eggs – ensuring they are fully incorporated before being introduced to the dry mixture.

• Whisk: A good whisk is indispensable for smoothly blending both the dry and wet ingredients separately, and then for gently combining them to form a cohesive, lump-free cake batter.

• Spatula: A flexible spatula is incredibly useful for scraping down the sides of the mixing bowl to ensure all batter is incorporated. It’s also perfect for gently spreading the cake batter evenly over the pineapple and cherry topping in the skillet, without disturbing the arrangement.

• Toothpick: A simple toothpick is your reliable indicator for cake doneness. Insert it into the very center of the cake; if it comes out clean, your cake is perfectly baked and ready.

• Serving Plate: Once the cake has cooled sufficiently in the skillet, a sturdy serving plate is required for the grand reveal – inverting the cake from the skillet to display its beautiful, caramelized fruit topping.

Use pre-sliced pineapple: Opting for canned pineapple slices is a huge time-saver, eliminating the need to peel, core, and slice a fresh pineapple, which can be messy and time-consuming.

Pre-measure ingredients: Embrace the “mise en place” philosophy by measuring out all your ingredients before you even start mixing. This streamlines the baking process, ensuring everything is ready when needed and preventing last-minute rushes.

Melt butter in microwave: Instead of waiting for butter to melt slowly on the stove, use the convenience of your microwave to quickly melt the butter in a microwave-safe bowl. This speeds up the creation of your caramel topping base.

Use a stand mixer: While mixing by hand is fine, utilizing a stand mixer with the paddle attachment can significantly speed up the blending process for the batter, ensuring a smooth and consistent mixture with less effort.

Preheat oven early: Make it a habit to start preheating your oven as soon as you begin gathering your ingredients. This way, the oven will be at the perfect temperature the moment your batter is ready, eliminating any waiting time.