Recipe

Simple Pineapple Upside Down Cake

A classic, juicy pineapple upside down cake with a buttery brown sugar topping, tender vanilla crumb, and crisp caramelized edges. No fancy ingredients, just reliable retro magic.

By Matt Campbell

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4.8

A freshly flipped pineapple upside down cake on a cake stand with glossy caramelized pineapple rings and cherries

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There are desserts that feel like a warm handshake, and pineapple upside down cake is one of them. It is sweet and sunny, with that sticky brown sugar topping that turns into a glossy caramel the second you flip the pan. The best part is the contrast: juicy pineapple on top, tender vanilla cake underneath, and those crisp, caramelized edges that make you “accidentally” cut a second slice.

This version keeps things simple and weeknight-friendly: canned pineapple, pantry staples, and clear steps that do not assume you were born holding a stand mixer. You just need a good pan, a little patience for the flip, and permission to lick the spoon if that is your thing (bonus points for doing it safely).

A slice of pineapple upside down cake on a plate showing the caramel topping and tender crumb

Why It Works

Juicy, glossy topping: Brown sugar and butter melt into a caramel that soaks slightly into the cake, in the best way.
Tender, not dry: Sour cream (or Greek yogurt) adds moisture and a soft crumb without making the cake heavy.
Crisp edges: Baking in a cast iron skillet or metal cake pan gives you those golden, toasty sides.
Low-drama flip: A short rest time lets the topping release cleanly so you get pretty rings, not pineapple chaos.

Pairs Well With

Storage Tips

Room temperature: Cover and keep for up to 24 hours in a cool room. If your kitchen runs warm, or if you want the safest, best-quality option, refrigerate.

Refrigerator: Store slices in an airtight container for up to 4 days. The topping will set a bit when cold, which is normal.

Freezer: Freeze individual slices wrapped tightly in plastic wrap, then foil, for up to 2 months. Thaw overnight in the fridge.

Reheat tip: Warm a slice in the microwave starting at 10 seconds, then add 5-second bursts as needed to loosen the caramel and bring back that just-baked vibe.

Common Questions

Do I have to use maraschino cherries?

Nope. They are classic and cute, but totally optional. If you want a less sweet option, try raspberries (add after baking) or just skip the fruit accents.

Can I use fresh pineapple instead of canned?

Yes, with one caveat: fresh pineapple is less uniform, and the juiciness and sweetness can be less consistent than canned (which is packed in juice or syrup). Slice it into 1/2-inch rings or thick half-moons. For best results, add a splash of pineapple juice or water to the topping (1 to 2 tablespoons) so the caramel stays saucy.

What pan works best?

A 10-inch cast iron skillet is the easiest and gives great browning. A 9-inch round metal cake pan also works well. Glass can work, but it tends to heat differently, so the cake may brown less and bake a bit unevenly.

Why did my cake stick?

Usually one of three things: the pan cooled too long, the caramel got too thick, or the pan was under-buttered. Butter the sides well, and flip while the cake is still warm.

How do I know it is done?

The top should spring back lightly when touched, and a toothpick inserted in the cake portion (not through pineapple) should come out clean or with a few moist crumbs. If it is browning too fast, tent loosely with foil.

Matt Campbell

I have always had a huge passion for the culinary arts, people, working as a team, and so on. I wanted to pursue my love for cooking initially at Virginia Commonwealth University with a culinary arts degree; however, I instead decided to apply myself and acquire more practical skills. My end goal is to eventually open my own restaurant or similar establishment.

Kitchen Essentials

10-inch cast iron skillet or 9-inch round metal cake pan
Mixing bowls
Whisk and rubber spatula
Measuring cups and spoons
Hand mixer or stand mixer (helpful, not required)
Cooling rack
Large plate or serving platter for flipping

I love pineapple upside down cake because it is a little dramatic in the most fun way. You do the work, you trust the process, and then you flip it like a kitchen magic trick. The first time I made it, I hovered over the pan like it owed me money, convinced the whole thing would stick. It did not. It slid out glossy and perfect, and I felt like I had unlocked some secret grandma-level power. Now it is my go-to when I want a dessert that looks impressive but is basically pantry baking plus one bold move: the flip.