Pineapple Upside-Down Cake

This is THE best easy Pineapple Upside-Down Cake from scratch!  Made with a soft, fluffy, and simple vanilla cake base that uses only the most basic ingredients and a pretty topping of caramelized pineapple and maraschino cherries, this classic recipe is slated to be a staple in your baking repertoire. It’s easy to prepare (even for beginners) and has received rave reviews!

If you follow my Instagram stories, you might be tired of seeing this pineapple upside-down cake already.  That’s because it took me so many attempts to get it right, and every time I thought I nailed it, I shared it on Instagram, and then it turned out that I hadn’t quite turned out like I’d hoped, after all.

Sorry about that.

It was the fluffy vanilla cake layer that was so difficult.  The pineapple and cherry top (/bottom?) is the easy part, it’s just a matter of combining melted butter and brown sugar in a pie plate and assembling your fruit, but a well-suited vanilla cake was much trickier to get right.

Can you believe that my biggest problem was that my cake started out being much too moist?

I wanted a cake layer that was reliable and would come out right every time. I needed it to be fluffy and soft, but it also needed to be sturdy enough that it could handle a little bit of weight on top once it was inverted, and not so moist that it absorbed all of the juices from the fruit, leaving you with a soggy sponge for a cake. It took me over 8 tries to get it right (and I ultimately used that base as the springboard for my perfect vanilla cake recipe!)

What You Need:

Our ingredient list is simple. You need:

• Pineapple rings. Fresh or canned will work.
• Maraschino cherries. Some readers have commented that they don’t like cherries. I don’t either, but they work very well here with pineapple upside-down cake. However, you can leave them out if you prefer.
• Butter. For both the pineapple/cherry base (top?) and the cake mix
• Sugar, granulated and brown, again for both the topping and the cake.
• Flour. This recipe uses all-purpose flour. Basic and easy!
• Milk. I use whole milk. I found buttermilk doesn’t work too well with this recipe, even though I love using it in others it actually makes the cake too moist.
• Eggs.
• Baking powder. It may seem like a lot but you need all of it!
• Salt. For flavor, of course.

The ratios took a while to perfect, but after some experimentation with eliminating the buttermilk and sour cream that I had been using in my recipe (and getting a bit friendlier with the baking powder than I initially was comfortable with), I finally achieved a stable, versatile, from-scratch vanilla cake layer that paired perfectly with the fruit topping and was not at all sponge-y.

In fact, since it was first published, I’ve received well over a hundred comments and emails from people telling me how much they love this cake, and I think you’re going to love it just as much.

How to flip a pineapple upside-down cake

In anticipation of a question I’m asked frequently about inverting cakes, I wanted to address the best way to flip your pineapple upside-down cake. Trust me, it’s extremely simple, but since the inversion part is so critical to this pineapple upside-down cake, I wanted to address that here.

1.  Allow your pineapple upside-down cake to cool for 10-15 minutes before you attempt inversion.  If any of the cake has baked into  the edge of your pie plate or cake pan, you can use a knife to gently loosen the edges and free them from the pan.
2. Place your cake platter (or any plate that’s larger than your cake) over the pan — plate surface should be facing your vanilla cake layer.
3. Using oven mitts (it will be hot!) carefully and firmly grip both the side of the cake platter and the cake pan on either side.
4. Carefully but quickly flip everything over so that the bottom of the cake pan is facing upwards, and then set down your cake platter and carefully remove the cake pan (careful, it will still be hot!)

And that is it!  This cake tastes best warm, so while you still want it to cool a bit, I don’t recommend waiting too long to dig in or making it very far in advance of serving!

Enjoy!

More Recipes You Might Like:

• Tres Leches Cake
• Coconut Cake
• Vanilla Cupcakes
• Creme Brulee
• Fresh Strawberry Cake

Are you more of a visual learner? Check out my YouTube channel where I show you exactly how I make this recipe in detail, step-by-step, in my own kitchen.

Pineapple Upside Down Cake

This recipe is not only a classic, it's super EASY to make and can be prepped in 25 minutes! Caramelized pineapple and cherries over a soft vanilla cake layer, this cake has hundreds of rave review!

4.93 from 399 votes

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Course: Dessert

Cuisine: American

Prep Time: 25 minutes

Cook Time: 45 minutes

Total Time: 1 hour 10 minutes

Servings: 8 slices

Calories: 433kcal

Author: Sam Merritt

Ingredients

Topping

• ▢ ¼ cup butter salted or unsalted melted (60g)
• ▢ ½ cup brown sugar light or dark (I usually use light) tightly packed (100g)
• ▢ 10 pineapple rings/slices patted dry
• ▢ maraschino cherries

Vanilla Cake

• ▢ ½ cup unsalted butter softened to room temperature (115g)
• ▢ ¾ cup sugar (150g)
• ▢ 2 eggs room temperature preferred
• ▢ 1 teaspoon vanilla extract
• ▢ 1 ½ cups all-purpose flour (195g)
• ▢ 1 ½ teaspoons baking powder
• ▢ ¼ teaspoon salt
• ▢ ½ cup milk room temperature preferred (120ml)

Recommended Equipment

• ▢
  Pie plate
• ▢
  Mixing bowls

Cook ModePrevent your screen from going dark

Instructions

• Preheat oven to 350F (175C)
• Pour melted butter into 9.5-10" pie plate or deep cake pan, make sure it entirely covers the bottom of the pan and use a spoon or spatula to grease the sides of the pan.
• Sprinkle brown sugar evenly over butter mixture.  Arrange pineapple slices over the bottom of the pan, slice leftover slices in half and arrange up the sides of the pan, as seen in photo.
  
• Place cherries in center of pineapple rings and as desired in empty spaces.  Set aside.
• To prepare vanilla cake, beat butter and sugar in medium-sized bowl until creamy and well-combined.  
• Add eggs, beating one at a time until combined.  
• Stir in vanilla extract.
• In a separate bowl, whisk together flour, baking powder, and salt.  
• Alternate adding flour and milk to the wet ingredients, starting and ending with flour and mixing until just combined after each addition (I prefer to do this part by hand with a spatula to be sure not to overmix).
• Pour batter evenly over prepared cake pan and pineapple/cherry layer.  
• Bake on 350F (175C) for 30 minutes.  At the 30 minute mark, loosely cover with foil and continue to bake (still on 350F/175C) for another 15 minutes, until a toothpick inserted in the center comes out mostly clean with few crumbs (total cook time for cake will be 45 minutes).
• Allow to cool for 10-15 minutes and then carefully invert cake onto serving platter (careful, it will still be very hot!).
• Allow to cool before cutting and enjoying, but don't wait too long as this cake tastes wonderful (best!) warm from the oven!

Notes

Pineapple Upside Down cake is best served fresh and warm (isn't everything, though).

Nutrition

Serving: 1slice | Calories: 433kcal | Carbohydrates: 62g | Protein: 5g | Fat: 19g | Saturated Fat: 12g | Cholesterol: 88mg | Sodium: 253mg | Potassium: 243mg | Fiber: 2g | Sugar: 43g | Vitamin A: 652IU | Vitamin C: 7mg | Calcium: 87mg | Iron: 2mg

Nutritional information is based on third-party calculations and should be considered an estimate only. Actual nutritional content will vary based upon brands used, measuring methods, cooking method, portion sizes, and more.

Tried this recipe? Show me on Instagram!Mention @SugarSpun_Sam or tag #sugarspunrun!

This post was originally published 06/22/2017 and is one of my best-loved recipes! Today I’m updating it with a few new helpful photos, a little more description in the text, and a new video. The recipe remains 100% the same, it’s perfect as-is!!