Cast Iron Skillet Pineapple Upside Down Cake Recipe (From Scratch)

Take a trip down memory lane with this Cast Iron Skillet Pineapple Upside Down Cake. It's a beautiful cake that's rich, buttery, and melt in your mouth delicious. Be sure to make this classic recipe to share with your family and friends that are sure to give it rave reviews. 

Updated May 2026: I've refreshed this post with new tips, expanded FAQs, a make-ahead section, and answers to all the questions y'all have been sending me. Originally posted on June 21, 2024.

Watch this quick video tutorial!

I cannot tell you the exact moment I fell in love with pineapple upside down cake, but I can tell you it smelled like my mother's kitchen. There was always a cast iron skillet involved, a little ring of golden pineapple, and that one cherry placed right in the middle like a tiny ruby. Before it flipped, it honestly didn't look like much, and then it did, and the whole table went quiet.

I've made this cake more times than I can count, and I tested this version until the cake came out tender and buttery every single time instead of dry the way so many recipes turn out. This is a true from-scratch cast iron skillet pineapple upside down cake. No boxed mix and the cast iron is what gives you that deep, caramelized brown sugar crust you just can't fake in a regular pan.

It's a showstopper that's secretly one of the easiest desserts you'll ever pull off, and I'm going to walk you through every step so yours flips out perfectly. Let's get started!

Why You'll Love This Cast Iron Skillet Pineapple Upside Down Cake

• Pure nostalgia - Buttery yellow cake under a glossy layer of caramelized pineapple and cherries tastes like Sunday dinner at grandma's.
• Made from scratch - No cake mix here, just simple pantry staples, and the flavor difference is real (you can still grab a shortcut in the Variations section if you're short on time).
• The cast iron magic - A seasoned skillet gives you a crisp, caramelized edge and releases the cake cleanly, so it slides right out onto your plate.
• Flexible and forgiving - Works in a 9-inch or 12-inch skillet, mixes by hand or by machine, and looks impressive with almost no effort.

Ingredients You'll Need 

Here's everything you'll need to make this recipe.

1. Butter - Does double duty here: it builds the caramel topping in the skillet and makes the cake itself rich and tender. Unsalted gives you the most control over the final sweetness.
2. Brown sugar - This is what turns into that sticky, caramelized layer over the pineapple. I reach for light brown sugar, but dark brown sugar works beautifully if you want a deeper, almost molasses-like edge.
3. Pineapple slices - The classic choice. Canned rings are easiest to arrange and bake up softer than fresh. Crushed pineapple works too (that's what my mom always used). See the Variations section for how to switch.
4. Maraschino cherries - One in the center of each ring for that signature pop of red and a little tart bite. If you go the crushed-pineapple route, you can leave these out.
5. All-purpose flour - Plain flour, nothing self-rising, for a cake with good structure that still stays soft.
6. Baking powder - Your lift. Check the date on the can, old baking powder is the number one reason a cake bakes up flat.
7. Granulated sugar, egg, whole milk, and vanilla - These build the actual cake batter. Whole milk keeps it moist, and pure vanilla (not imitation) makes a noticeable difference in a cake this simple.

👉🏾 See the recipe card below for exact quantities and full instructions.

How to Make Cast Iron Skillet Pineapple Upside Down Cake

Here's a quick overview of the process. Full step-by-step instructions are in the recipe card below.

Step 1: Build the caramel right in the skillet

Melt the butter in your cast iron skillet over medium heat, then stir in the brown sugar and a splash of the reserved pineapple juice until the sugar dissolves into a glossy caramel. Doing this directly in the skillet instead of just sprinkling dry sugar is the secret to an even, set caramel that doesn't pool in the middle.

Step 2: Arrange the pineapple and cherries

Pull the skillet off the heat and lay your pineapple rings over the caramel, then tuck a cherry into the center of each. Work from the outside in so the pattern looks intentional. This is the side everyone sees, so take your thirty seconds here.

Step 3: Mix the batter without overworking it

Cream the butter and sugar until truly light and fluffy (a full 2-3 minutes), then add your wet ingredients, and finally the flour mixture. Mix just until it comes together. Overmixing once the flour goes in is what makes a cake tough and dry, so stop as soon as you don't see streaks.

Step 4: Pour, bake, and flip

Spoon the batter gently over the pineapple and smooth it level without disturbing the fruit underneath. Bake until a tester comes out clean, then, and this is the important part, let it cool just 10 to 15 minutes before inverting. Too soon and it falls apart; too long and the caramel glues itself to the pan.

LaKita's Expert Tips

Here are my best tips for making this recipe turn out perfectly every time.

• Loosen before you flip. Run a thin knife all the way around the edge of the cake before inverting, this is cheap insurance against a stuck edge.
• Don't skip the cool-down window, but don't overdo it. Ten to fifteen minutes is the sweet spot. The caramel needs to set slightly but still be warm enough to release.
• Room-temperature ingredients matter. Cold egg and milk fight the creamed butter and give you a denser cake. Let them sit out 30 minutes first.
• Bring your serving plate to the skillet, not the other way around. Place the plate over the skillet, hold them together firmly, and flip in one confident motion. Hesitation is what makes cakes slide.
• Watch the edges, not the clock. Ovens vary; pull the cake when a tester comes out with a few dry crumbs and the edges just start pulling from the pan.
• Catch the drips. Set your skillet on a rimmed baking sheet in the oven. A full skillet can bubble over, and caramel on the oven floor is no fun to clean.
• A 12-inch skillet bakes faster. The thinner cake layer in a larger skillet sets sooner, so start checking 5 minutes early.

Variations & Substitutions

This recipe is flexible, here are some easy ways to make it your own.

• Crushed pineapple instead of rings - Spread well-drained crushed pineapple over the caramel for a more rustic look. You can skip the cherries or scatter them in.
• Fresh pineapple - Slice it thick and pat it dry. It's a little firmer than canned, so the rings hold their shape beautifully.
• Boxed cake mix shortcut - Short on time? Prepare the skillet caramel and pineapple from scratch, then top with a prepared yellow cake mix batter. You'll still get the cast iron crust with less effort.
• Add warm spice - A pinch of cinnamon or ground ginger in the batter plays gorgeously against the caramelized pineapple.
• Swap the milk for buttermilk - For a slightly tangier, extra-tender crumb.
• Make it boozy - A tablespoon of dark rum in the batter leans this toward a grown-up tropical dessert.

Make-Ahead & Storage

Make-Ahead

This cake is at its absolute best the day it's made, but you can get ahead a little. Measure and whisk your dry ingredients the night before, and have your pineapple drained (save that juice for the caramel) and cherries patted dry. You can also bake the full cake earlier in the day and flip it a few hours before serving, just leave it loosely covered at room temperature.

Storage & Reheating

Storage. Once fully cooled, store the cake at room temperature for 1 to 2 days in an airtight container or tightly wrapped. In warm weather or for longer keeping, refrigerate up to 4 days and bring slices back to room temperature before serving. To freeze, wrap the fully baked cake well and store up to 1 month, then thaw overnight in the fridge, though I'll be honest, the texture is best fresh.

Reheating. To bring back that just-baked warmth, reheat individual slices in a 325°F oven or toaster oven on a parchment-lined sheet for 5 to 10 minutes until the caramel softens. A 15-20 second zap in the microwave works in a pinch but won't re-crisp the edges the way the oven does.

What to Serve with Cast Iron Skillet Pineapple Upside Down Cake

Here are some of my favorite ways to serve this dish.

• With a drizzle of the leftover skillet caramel spooned over the top for anyone with a serious sweet tooth.
• A warm slice with a scoop of vanilla ice cream or a cloud of fresh whipped cream. The cold against the warm caramel is everything.
• Alongside a pot of coffee for an afternoon treat, it pairs beautifully with my Hummingbird Coffee Cake on a weekend baking spread.
• As part of a Southern dessert table next to a Homemade Sour Cream Pound Cake and a fruit cobbler.
• For a tropical-themed gathering, serve it after a round of Pineapple Tarts with Puff Pastry to keep the pineapple theme going.

Frequently Asked Questions