Old-Fashioned Pineapple Upside-Down Cake (Classic Easy Recipe)

This old-fashioned pineapple upside-down cake has a buttery brown-sugar topping, glossy pineapple rings, and a soft vanilla cake underneath. It looks special when turned out onto a serving plate, but the method uses familiar pantry ingredients and a single round cake pan.

For the cleanest finish, arrange the pineapple before adding the batter, measure the flour carefully, and let the cake rest briefly after baking. Invert it while still warm enough for the topping to release, using oven mitts and a plate larger than the pan.

Recipe at a Glance

Prep: 20 minutes
Bake: 40–45 minutes
Total: about 1 hour 5 minutes
Serves: 8
Pan: 9-inch round cake pan

Ingredients

For the topping

1/4 cup (56 g) unsalted butter, melted
2/3 cup (135 g) packed light brown sugar
7–8 canned pineapple rings, drained well
Maraschino cherries, optional

For the cake

1 1/2 cups (190 g) all-purpose flour, spooned and leveled
1 1/2 teaspoons baking powder
1/4 teaspoon fine salt
1/2 cup (113 g) unsalted butter, softened
2/3 cup (135 g) granulated sugar
2 large eggs, room temperature
1 teaspoon vanilla extract
1/2 cup (120 ml) whole milk, room temperature

Note: Ingredient measurements by weight: visit King Arthur Baking

Equipment

9-inch round cake pan, mixing bowls, hand mixer or stand mixer, whisk, spatula, measuring tools, and a heat-safe serving plate.

Instructions

1. Prepare the pan and oven

Heat the oven to 350°F (175°C). Lightly grease the sides of a 9-inch round cake pan. Set the pan on a baking sheet in case a little topping bubbles over.

2. Make the pineapple topping

Pour the melted butter into the pan and spread it evenly. Sprinkle the brown sugar over the butter. Arrange drained pineapple rings in a single layer; place a cherry in the center of each ring if using. Blot excess juice from the pineapple with paper towels to reduce sogginess.

3. Combine the dry ingredients

Whisk flour, baking powder, and salt in a medium bowl until evenly combined.

4. Cream butter and sugar

In a separate bowl, beat the softened butter and granulated sugar for 2–3 minutes until lighter and fluffy. Beat in the eggs one at a time, then mix in vanilla. Scrape down the bowl as needed.

5. Finish the batter

Add the flour mixture in three additions, alternating with the milk in two additions, beginning and ending with flour. Mix on low just until no dry streaks remain. Do not overmix.

6. Fill the pan and bake

Spoon the batter carefully over the pineapple and smooth the top. Bake for 40–45 minutes, until golden and a toothpick inserted into the cake portion comes out clean or with a few moist crumbs.

7. Rest, invert, and cool

Let the cake rest in the pan for 8–10 minutes. Run a thin knife around the edge. Place a large serving plate over the pan, hold both securely with oven mitts, and invert in one controlled motion. Leave the pan in place for about 30 seconds, then lift it away carefully. If a pineapple ring sticks, reposition it while the topping is still warm. Cool before slicing.

Pineapple rings and cherries arranged over brown sugar butter topping in a cake pan

Tips for a Beautiful Cake

Drain and blot canned pineapple well; excess liquid can make the topping watery.
Use room-temperature eggs and milk so the batter combines evenly.
Measure flour by weight when possible, or spoon it into the measuring cup and level the top.
Do not wait until the cake is completely cold to invert it; the brown-sugar topping can harden and stick.
Use a plate with a rim to catch the buttery topping.

Variations

Use pineapple tidbits: arrange small pieces in a decorative layer, keeping them well drained.
Add coconut: sprinkle 2 tablespoons of unsweetened shredded coconut over the topping before adding batter.
Warm spice: add 1/4 teaspoon ground cinnamon to the dry ingredients.
Brown-butter flavor: brown the topping butter, then cool it slightly before using.

Serving Suggestions

Serve slices at room temperature or slightly warm. A small spoonful of lightly whipped cream or vanilla ice cream pairs well with the caramelized pineapple.

Storage

Cover the cooled cake and refrigerate for up to 4 days because of its moist fruit topping. Bring slices closer to room temperature before serving, or warm briefly. For longer storage, freeze individual slices tightly wrapped for up to 2 months; thaw overnight in the refrigerator.

Frequently Asked Questions

Can I use fresh pineapple?

Yes, if it is ripe and sliced evenly. Canned rings are more consistent in moisture and shape, so fresh pineapple may need extra blotting and can produce a slightly different topping.

Why did my cake stick to the pan?

The topping may have cooled and hardened, or the pan may not have been greased at the sides. Rest the cake for about 8–10 minutes, loosen the edges, and invert while warm. Avoid leaving it in the pan for too long.

How can I tell when the cake is done?

The top should be golden and spring back lightly when touched, and a toothpick inserted into the cake portion should come out clean or with a few moist crumbs. Avoid testing only in a pineapple section.

Can I make it a day ahead?

Yes. Bake and invert the cake, cool completely, cover, and refrigerate. The topping stays moist; let the cake sit at room temperature briefly before serving.

Slice of pineapple upside-down cake showing tender vanilla crumb and caramelized pineapple topping

Recipe Summary

This old-fashioned pineapple upside-down cake layers pineapple and brown sugar beneath a tender vanilla butter cake. Bake in a 9-inch round pan, rest briefly, then invert while warm for a glossy fruit topping.

Kitchen note: Oven temperatures and pan materials vary. Begin checking near 40 minutes and allow the cake to finish baking if the center is not set.