Pineapple Upside Down Pound Cake Recipe | Classic Dessert Reinvented

Venturing beyond the traditional skillet preparation, this pineapple upside down pound cake elevates the classic American dessert through precise baking techniques and ingredient balance. Visualize golden caramelized pineapple rings embedded in a rich, buttery pound cake that maintains structural integrity while delivering exceptional moisture and flavor complexity. This professional approach transforms familiar components into a sophisticated baked good worthy of any culinary showcase.

Why This Recipe Works

• The reverse creaming method, where butter is incorporated into dry ingredients before adding liquids, creates an exceptionally fine crumb structure that prevents tunneling and ensures even distribution of the pineapple caramel throughout the cake batter during baking.
• Using both granulated sugar in the caramel layer and light brown sugar in the cake batter provides dual sweetness profiles—the former creating that essential crisp caramelization while the latter contributes molasses notes that complement the tropical fruit flavors.
• Full-fat sour cream introduces tanginess that cuts through the sweetness while its fat content and acidity work to tenderize the gluten development, resulting in a pound cake with superior moisture retention and a velvety texture that doesn’t become gummy.
• Precise oven temperature management with a starting high heat to set the structure followed by reduced temperature baking prevents over-browning of the caramel topping while ensuring the dense pound cake batter cooks through without developing a dry exterior.
• The strategic placement of maraschino cherries within the pineapple rings isn’t merely decorative—their syrup contributes additional moisture to the caramel layer and their bright color provides visual contrast that indicates proper doneness when the cake is inverted.

Ingredients

• 1/2 cup unsalted butter, melted (for caramel layer)
• 1 cup light brown sugar, packed (divided: 1/2 cup for caramel, 1/2 cup for batter)
• 1 can (20 ounces) pineapple rings in juice, drained with 1/4 cup juice reserved
• 8-10 maraschino cherries, thoroughly patted dry
• 2 cups all-purpose flour, spooned and leveled
• 1 teaspoon baking powder
• 1/2 teaspoon baking soda
• 3/4 teaspoon fine sea salt
• 1 cup granulated sugar
• 1 cup unsalted butter, softened to 68°F (for cake batter)
• 4 large eggs, at room temperature (65-70°F)
• 1 teaspoon pure vanilla extract
• 1/2 teaspoon almond extract
• 1 cup full-fat sour cream, at room temperature

Equipment Needed

• 10-inch tube pan or 9×13-inch baking pan
• Stand mixer with paddle attachment
• Digital kitchen scale
• Instant-read thermometer
• Medium saucepan
• Wire cooling rack
• Offset spatula
• Parchment paper

Instructions

Prepare the Caramel Pineapple Base

Begin by preheating your oven to 350°F and generously buttering your tube pan, ensuring all crevices are thoroughly coated to prevent sticking. In a medium saucepan over medium heat, combine the 1/2 cup melted butter with 1/2 cup packed light brown sugar, whisking continuously until the sugar fully dissolves and the mixture becomes smooth and bubbly, approximately 3-4 minutes. Remove from heat and immediately pour this caramel into the bottom of your prepared pan, using an offset spatula to spread it into an even layer. Arrange the drained pineapple rings in a single layer over the caramel, placing one maraschino cherry in the center of each ring. The cherries should be thoroughly patted dry to prevent moisture from disrupting the caramel structure. Professional tip: Work quickly while the caramel is still fluid to achieve perfect placement, as it will begin to set within minutes at room temperature.

Combine Dry Ingredients and Cream Butter Mixture

In the bowl of your stand mixer fitted with the paddle attachment, combine the all-purpose flour, remaining 1/2 cup light brown sugar, granulated sugar, baking powder, baking soda, and sea salt. Mix on low speed for 30 seconds to aerate and evenly distribute the leavening agents throughout the flour. With the mixer running on low, add the softened butter one tablespoon at a time, allowing each addition to incorporate before adding the next. Continue mixing until the mixture resembles coarse sand with no visible butter chunks, approximately 2-3 minutes. This reverse creaming method coats the flour proteins with fat, limiting gluten development and resulting in a finer, more tender crumb structure than traditional creaming methods. The mixture should hold together when pressed between your fingers but easily break apart.

Incorporate Wet Ingredients and Develop Batter

In a separate medium bowl, whisk together the room-temperature eggs, vanilla extract, almond extract, and reserved pineapple juice until thoroughly combined and slightly frothy. With the mixer on medium-low speed, gradually add the egg mixture to the butter-flour mixture in three separate additions, scraping down the bowl with a rubber spatula between each incorporation. Once the eggs are fully incorporated, add the room-temperature sour cream in two additions, mixing just until combined after each. The batter should be thick, smooth, and creamy with no streaks of sour cream visible. Professional tip: Room temperature ingredients emulsify more effectively, creating a stable emulsion that will result in even rising and a uniform texture throughout the baked cake.

Assemble and Begin Baking Process

Carefully spoon the batter over the arranged pineapple and caramel layer in your prepared pan, using an offset spatula to gently spread it into an even layer without disturbing the fruit arrangement. Tap the pan firmly on the countertop several times to release any large air bubbles that could create tunnels in the finished cake. Place the pan in the preheated 350°F oven on the center rack and bake for 20 minutes. After this initial period, reduce the oven temperature to 325°F without opening the oven door. This two-temperature approach sets the cake’s structure quickly while allowing the interior to bake through without over-browning the caramel topping.

Complete Baking and Test for Doneness

Continue baking at 325°F for an additional 45-55 minutes, rotating the pan halfway through to ensure even browning. Begin testing for doneness at the 45-minute mark by inserting an instant-read thermometer into the center of the cake—it should register between 200-210°F. Additionally, a wooden skewer inserted into the center should come out with a few moist crumbs attached but no wet batter. The cake should be golden brown and beginning to pull away slightly from the sides of the pan. The caramel around the edges should be actively bubbling but not burning—if the edges appear to be darkening too quickly, tent the pan loosely with aluminum foil.

Cool and Invert the Finished Cake

Immediately upon removal from the oven, run a thin knife or offset spatula around the edges of the pan to loosen any areas where the caramel may have adhered during baking. Place a wire cooling rack over the pan, then carefully but confidently invert the pan and rack together. Allow the cake to rest in this position for 5 minutes to let gravity work—this gives the caramel time to release from the pan but not so long that it sets completely. Gently lift the pan straight up rather than at an angle to preserve the decorative pineapple pattern. Professional tip: If any pineapple rings stick to the pan, carefully reposition them while the caramel is still warm and pliable.

Final Cooling and Service Preparation

Allow the cake to cool completely on the wire rack for at least 2-3 hours before slicing. During this cooling period, the caramel will set properly and the cake structure will firm up, making clean slices possible. For optimal texture and flavor development, the cake benefits from resting overnight—wrap it tightly in plastic wrap once completely cool and serve at room temperature the following day. When ready to serve, use a serrated knife dipped in hot water and wiped dry between cuts to achieve clean slices that showcase the beautiful pineapple pattern. The cake maintains optimal texture for 3-4 days when stored in an airtight container at room temperature.

Tips and Tricks

For professional-level results, consider these advanced techniques that build upon the foundation of the basic recipe. When selecting pineapple, opt for rings packed in juice rather than heavy syrup—the natural acidity balances the sweetness more effectively. If using fresh pineapple, poach the rings in a simple syrup (1:1 ratio sugar to water) for 10 minutes to tenderize the fruit and prevent enzyme activity that can interfere with proper setting of the caramel layer. For enhanced flavor complexity, infuse your caramel with a split vanilla bean during the melting process or add a tablespoon of dark rum to the finished caramel before pouring it into the pan. Temperature control extends beyond ingredient preparation—ensure your oven is properly calibrated using an independent oven thermometer, as even a 25°F variance can significantly impact the cake’s texture and caramelization. When testing for doneness, rely more on internal temperature (200-210°F) than visual cues alone, as the dark caramel can mask visual indicators of proper baking. For exceptionally clean release, line the bottom of your pan with a parchment round before adding the caramel—this provides insurance against sticking while still allowing the caramel to properly adhere to the cake during inversion. If your cake develops significant doming during baking, use a serrated knife to level the bottom (which becomes the top after inversion) while the cake is still slightly warm—this creates a stable base for serving. For professional presentation, brush the finished cooled cake with a thin layer of warmed apricot preserves thinned with a teaspoon of water—this creates a beautiful glossy finish that enhances the visual appeal while adding minimal additional sweetness. When storing leftovers, place parchment paper between slices to prevent them from sticking together, and note that the caramel will continue to absorb into the cake over time, creating an even more moist texture by the second day.

Recipe Variations

• For a tropical twist, replace half the vanilla extract with coconut extract and add 1/2 cup toasted sweetened coconut flakes to the batter. The coconut’s natural oils complement the pineapple’s acidity while adding textural interest. Toast the coconut at 325°F for 5-7 minutes until golden brown before incorporating to enhance its nutty flavor profile and ensure crispness that withstands the baking process.
• Create an adult version by soaking the pineapple rings in 2 tablespoons of dark rum or spiced whiskey for 30 minutes before assembling. The alcohol will mostly bake out while leaving behind complex flavor notes that pair exceptionally well with the brown sugar caramel. For additional sophistication, brush the finished cake with a rum simple syrup (equal parts rum and sugar heated until dissolved) after cooling.
• Transform this into a citrus-infused variation by adding the zest of one orange and one lemon to the cake batter. The citrus oils brighten the rich pound cake and provide a refreshing counterpoint to the sweet pineapple. For additional complexity, replace the maraschino cherries with fresh cranberries that have been tossed in granulated sugar—their tartness creates a delightful contrast with the sweet caramel.
• For a nutty interpretation, sprinkle 1/2 cup of finely chopped pecans or macadamia nuts over the caramel layer before adding the pineapple rings. The nuts toast in the caramel during baking, developing deep flavor and adding crunch that contrasts with the soft cake texture. Toast the nuts beforehand at 350°F for 8-10 minutes to enhance their natural oils and ensure they don’t become soggy during baking.
• Create individual portions using a standard 12-cup muffin tin lined with parchment liners. Divide the caramel among the cups, place a pineapple ring (or half-ring for smaller cups) in each, then fill 2/3 full with batter. Reduce baking time to 22-28 minutes at 350°F until a tester comes out clean. These individual cakes offer elegant presentation and controlled portion sizes for gatherings.

Frequently Asked Questions

Can I make this recipe in a different pan size than specified?

Yes, though adjustments will be necessary. For a 9×13-inch rectangular pan, reduce baking time by 10-15 minutes and check for doneness starting at 35 minutes. The shallower depth means the cake will bake more quickly but may have a slightly different texture. For Bundt pans, increase the caramel by 50% to ensure proper coverage of the intricate design, and be particularly diligent about greasing every crevice. Springform pans can work but require wrapping the bottom in aluminum foil to prevent caramel leakage during baking. Regardless of pan choice, maintain the same internal temperature target of 200-210°F for proper doneness.

Why did my pineapple upside down cake stick to the pan?

Sticking typically results from insufficient pan preparation, improper cooling time, or weak caramel structure. Ensure your pan is thoroughly greased with butter—pay special attention to corners and designs. The caramel must be hot when poured into the pan to properly adhere to the surface. Most importantly, invert the cake while it’s still warm (after 5 minutes of cooling) as the caramel will reset as it cools completely. If sticking occurs, return the pan to a warm oven for 2-3 minutes to gently rewarm the caramel before attempting to invert again. Using a non-stick pan specifically designed for sticky desserts can also improve release.

Can I prepare components of this cake in advance?

Yes, with proper technique. The caramel layer can be prepared up to 2 days ahead and stored covered at room temperature—gently reheat until fluid before assembling. The dry ingredients can be mixed and stored in an airtight container for up to one week. The complete batter should be used immediately after mixing for optimal rise, but you can measure all ingredients ahead for efficient assembly. The fully baked cake actually improves when made a day ahead—the flavors meld and the texture becomes more uniform. Wrap cooled cake tightly in plastic wrap and store at room temperature.

How can I tell when my pound cake is properly baked without overbaking?

Use multiple indicators for accuracy. The internal temperature should register 200-210°F on an instant-read thermometer inserted into the center—this is the most reliable method. Visually, the cake will pull away slightly from the pan edges, and the surface will spring back when gently pressed. A wooden skewer inserted into the center should emerge with a few moist crumbs attached rather than clean (which indicates overbaking) or with wet batter (underbaking). The caramel around the edges should be bubbling actively. Remember that residual heat will continue cooking the cake slightly after removal from the oven, so remove it when it’s just at the lower end of done.

Can I use fresh pineapple instead of canned, and what adjustments are needed?

Fresh pineapple requires additional preparation but offers superior flavor. Peel and core a ripe pineapple, then slice into 1/2-inch thick rings. Poach the rings in a simple syrup (1 cup sugar to 1 cup water) for 8-10 minutes until slightly translucent—this deactivates enzymes that can prevent proper setting and tenderizes the fruit. Drain thoroughly and pat dry before using. Fresh pineapple contains more moisture, so you may need to extend baking time by 5-10 minutes and watch carefully for proper caramelization. The result will be brighter, more complex pineapple flavor with better textural integrity than canned varieties.

Summary

This professional pineapple upside down pound cake masterfully balances technique and tradition through reverse creaming, precise temperature control, and strategic ingredient selection. The result showcases caramelized pineapple embedded in a velvety, moist pound cake with structural integrity and complex flavor development that improves with resting.

Louise Cutler

I’m Louise Cutler, a food lover who enjoys creating simple, flavorful recipes that anyone can make and share at home.