Classic Pineapple Upside-Down Cake

Name: Classic Pineapple Upside-Down Cake
Prep time: 30 min
Cook time: 45 min
Total time: 1 h 15 min
Yield: 8 servings
Cuisine: American
Ingredients: 6 tbsp (85 g) unsalted butter, cut into pieces; ¾ cup, packed (150 g) light brown sugar, packed, any lumps broken up; 7 rings (220 g) canned pineapple rings in juice, drained (juice reserved) and patted very dry with paper towels; 7 cherries (35 g) maraschino cherries, stemless, drained and patted dry; 1½ cups (190 g) all-purpose flour, spooned into the cup and leveled; 1½ tsp (6 g) baking powder; ¼ tsp (1½ g) fine salt; ½ cup (1 stick) (113 g) unsalted butter, at room temperature, soft enough to dent easily with a finger; ¾ cup (150 g) granulated sugar; 2 large (100 g) large eggs, at room temperature; 1 tsp (5 ml) pure vanilla extract; ¼ cup (60 ml) whole milk, at room temperature; ¼ cup (60 ml) pineapple juice, reserved from the canned pineapple, at room temperature

From the MyKitchenBank Kitchen

A buttery vanilla cake baked over a layer of brown sugar caramel, pineapple rings, and glossy maraschino cherries. Flipped out of the pan, it reveals a jewel-like, sticky-sweet top and a tender, moist crumb.

Prep: 30 min
Cook: 45 min
Wait: 20 min
Total: 1 hr 35 min
Makes: 1 9-inch (23 cm) round cake (8 slices)

Jump to recipe ♡ Save

Ingredients

8 servings

For the topping
6 tbsp (85 g) unsalted butter, cut into pieces
¾ cup, packed (150 g) light brown sugar, packed, any lumps broken up
7 rings (220 g) canned pineapple rings in juice, drained (juice reserved) and patted very dry with paper towels
7 cherries (35 g) maraschino cherries, stemless, drained and patted dry
For the cake
1½ cups (190 g) all-purpose flour, spooned into the cup and leveled
1½ tsp (6 g) baking powder
¼ tsp (1.5 g) fine salt
½ cup (1 stick) (113 g) unsalted butter, at room temperature, soft enough to dent easily with a finger
¾ cup (150 g) granulated sugar
2 large (100 g) large eggs, at room temperature
1 tsp (5 ml) pure vanilla extract
¼ cup (60 ml) whole milk, at room temperature
¼ cup (60 ml) pineapple juice, reserved from the canned pineapple, at room temperature

Equipment (13)

9×2-inch (23×5 cm) round metal cake pan
Small saucepan
Large mixing bowl
Medium mixing bowl
Electric hand mixer or stand mixer with paddle
Rubber spatula
Whisk
Paper towels
Thin knife or small offset spatula for loosening
Serving plate larger than 9 inches (23 cm), with a rim if possible
Rimmed baking sheet to set under the pan (catches drips)
Wire rack
Oven mitts

Steps

Before you start

Take the butter, eggs, and milk out of the fridge about 1 hour ahead so they reach room temperature (about 68°F / 20°C). This gives a smooth batter and an even crumb.
Use a 9×2-inch (23×5 cm) metal round pan with solid sides, not a springform pan. The caramel is liquid and will leak from a springform.
Buy canned pineapple rings packed in juice (not heavy syrup). You need 7 rings and about ¼ cup (60 ml) of the juice.
Place the oven rack in the center position and preheat to 350°F (175°C) before you begin.

1
Prep oven and fruitOven 350°F / 175°C
- Position a rack in the center of the oven and preheat to 350°F (175°C).
- Open the can of pineapple and pour the juice into a measuring cup; measure out ¼ cup (60 ml) for the batter and set it aside.
- Lay the 7 pineapple rings and the 7 cherries on a double layer of paper towels and blot the tops firmly.
- Dry fruit helps the caramel cling instead of turning watery.
+ Show details− Hide details
Ready when: Oven is fully preheated and the fruit feels tacky-dry, not wet, when touched.
Tip: Keep the leftover juice to drink or use in a glaze. Don't use more than ¼ cup in the batter or the cake can turn gummy.
2
Make caramel topping
- Melt the 6 tbsp (85 g) topping butter in a small saucepan over medium-low heat.
- Add the brown sugar and stir with a spatula for 2 to 3 minutes, just until the mixture is smooth, bubbling gently around the edges, and no gritty sugar remains.
- Pour it into the 9×2-inch (23×5 cm) cake pan and tilt the pan so it spreads in an even layer over the bottom.
+ Show details− Hide details
Ready when: The caramel is smooth, glossy, and sugar granules have dissolved.
Tip: Don't boil the mixture. Boiling can make the caramel too hard to release after baking.
3
Arrange the fruit
- Place one pineapple ring in the center of the caramel and arrange the other 6 rings around it, slightly touching, so they form a ring against the pan's edge.
- Press a cherry into the hole of each ring.
- Set the pan on a rimmed baking sheet.
+ Show details− Hide details
Ready when: The rings sit flat and snug against the caramel with no large gaps.
Tip: If the rings don't fit perfectly, trim one to fill gaps. The fruit will shift slightly in the oven, so a snug fit looks best.
4
Whisk dry ingredients
- In a medium bowl, whisk together the flour, baking powder, and salt for about 20 seconds until evenly combined.
- In a measuring cup, stir the milk and the ¼ cup (60 ml) reserved pineapple juice together.
- It may look slightly curdled from the juice's acidity; this is fine.
+ Show details− Hide details
Ready when: No streaks of baking powder remain in the flour.
5
Cream butter and sugar
- In a large bowl, beat the room-temperature butter and granulated sugar with an electric mixer on medium-high speed for 3 minutes, scraping the bowl halfway through, until the mixture is pale yellow, fluffy, and noticeably increased in volume.
+ Show details− Hide details
Ready when: The mixture is pale, fluffy, and looks like thick frosting, with no visible sugar crystals.
Tip: Cold butter won't trap air. If it is still cool, cream it an extra minute.
6
Beat in eggs and vanilla
- Add the eggs one at a time on medium speed, beating for 30 seconds after each and scraping the bowl.
- Beat in the vanilla.
- The batter should look smooth and thick.
+ Show details− Hide details
Ready when: The mixture is smooth and uniform, with no slick pools of egg.
Tip: If it looks curdled, keep mixing on medium for 20 seconds. It will come together once the flour goes in.
7
Fold in flour and liquid
- With the mixer on low, add the flour mixture in three parts, alternating with the milk-juice mixture in two parts, beginning and ending with flour (flour, liquid, flour, liquid, flour).
- Mix just until each addition disappears.
- Finish by folding once or twice with a spatula, scraping the bottom of the bowl.
+ Show details− Hide details
Ready when: The batter is thick, smooth, and spoonable, with no dry flour streaks.
Tip: Stop mixing as soon as the flour disappears. Overmixing makes the cake tough.
8
Fill pan and bakeOven 350°F / 175°C
- Dollop the batter over the fruit in spoonfuls, then gently spread it to the edges with an offset spatula or the back of a spoon, taking care not to drag the pineapple out of place.
- Bake the pan on its baking sheet at 350°F (175°C) for 40 to 45 minutes.
+ Show details− Hide details
Ready when: The top is deep golden brown, springs back when lightly pressed, and a toothpick inserted in the center comes out clean or with a few dry crumbs. Caramel will be bubbling at the edges.
Tip: If the top browns too fast before 35 minutes, loosely tent with foil.
9
Cool briefly, then flip
- Set the pan on a wire rack and cool for exactly 10 minutes.
- Run a thin knife around the edge of the cake.
- Place the serving plate upside down over the pan.
- Holding both firmly with oven mitts, flip them over in one confident motion.
- Leave the pan in place for 1 minute, then lift it off slowly.
- Nudge any stray fruit or caramel back into place with a spoon.
+ Show details− Hide details
Ready when: The pan lifts away cleanly and the pineapple and caramel are intact on top.
Tip: Don't wait longer than 15 minutes or the caramel will harden and stick to the pan. If it does, warm the bottom of the pan briefly on a burner for 20 seconds.
10
Rest and serve
- Let the cake rest on the plate for 10 minutes so the glossy caramel sets slightly and the crumb finishes firming.
- Slice into 8 wedges using a serrated knife and serve warm or at room temperature.
+ Show details− Hide details
Ready when: The caramel looks glossy and tacky, not runny.
Tip: A bit of whipped cream or vanilla ice cream balances the sweetness.

Good to know

Tips

Blot the fruit well. Extra moisture thins the caramel and can make the cake soggy on top.
Time the flip carefully: 10 minutes of cooling is the sweet spot for clean release.
Set the pan on a rimmed baking sheet in the oven to catch any bubbling caramel and keep your oven clean.
Check the cake at 40 minutes; ovens vary, and the cake should be golden, springy, and pass the toothpick test.

Make ahead

"Bake the cake up to 1 day ahead, flip it onto a plate, cool completely, then cover and keep at room temperature. Warm individual slices briefly before serving. You can also make the caramel and arrange the fruit in the pan up to 2 hours ahead; hold at room temperature, then add batter and bake."

Storage & reheating

"Room temperature: covered, up to 2 days. Refrigerator: up to 5 days in an airtight container; bring to room temperature or warm slices in a 300°F (150°C) oven for 8 to 10 minutes, or microwave for 15 to 20 seconds. Freezer: wrap individual slices tightly and freeze up to 2 months; thaw overnight in the fridge before reheating."

Substitutions

canned pineapple rings in juice → fresh pineapple, sliced into ⅓-inch (8 mm) rings with the core removed. Pat dry well and expect slightly more moisture; use the same ¼ cup of any pineapple juice from a carton for the batter.
maraschino cherries → pecan halves or dried tart cherries. Pecans add crunch; dried cherries add a tangy contrast. Use about 7 pieces or 1 tbsp in each ring.
light brown sugar → dark brown sugar. Gives a deeper, more molasses-like caramel flavor.
whole milk → buttermilk. Use the same amount; it adds tang and the baking powder will still work well.