Delicious homemade pineapple upside down cake made with cake mix, topped with caramelized pineapple rings and cherries.

Best Pineapple Upside Down Cake Recipe With Cake Mix (5 Tips!)

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Looking for a dessert that’s equal parts easy and impressive? This pineapple upside down cake recipe with cake mix is your answer! With just a handful of ingredients and 5 genius tips, you’ll create a retro treat that’s bursting with caramelized pineapple, juicy cherries, and fluffy cake. Whether you’re a baking newbie or a pro, this recipe guarantees golden edges, zero stress, and serious bragging rights. Let’s dive in!

Table of Contents

pineapple upside down cake recipe with cake mix

Ingredients You’ll Need


Here’s what you’ll need for this pineapple upside down cake recipe with cake mix:

  • 1 box yellow cake mix (plus ingredients listed on the box: eggs, oil, water)
  • 1/2 cup unsalted butter (melted)
  • 1 cup dark brown sugar
  • 1 can pineapple rings (20 oz, drained)
  • 8-10 maraschino cherries (no stems)
  • Optional upgrades: 1 tsp vanilla extract, 1/4 cup pineapple juice

Substitutions:

  • Gluten-free? Swap in a gluten-free cake mix.
  • Fresh pineapple? Precook slices in a skillet with sugar to soften.
  • No cherries? Use cranberries or skip them.

Essential Tools for Success
You don’t need fancy gadgets, but these tools make life easier:

  1. 9-inch cast-iron skillet or cake pan: Non-stick is key! A skillet ensures even caramelization.
  2. Mixing bowls: One for the batter, one for the topping.
  3. Spatula: To spread batter without messing up your pineapple design.
  4. Cooling rack: Lets air circulate so the cake doesn’t get soggy.

Why the pan matters: A well-greased pan prevents sticking (we’ll cover this in Tip #1!).

Step-by-Step Instructions

Step 1: Prep Your Pan (The Golden Rule)

  1. Melt 1/2 cup butter and pour it into your skillet or pan.
  2. Sprinkle 1 cup dark brown sugar evenly over the butter—this creates the caramel layer!
  3. Arrange pineapple rings in a single layer, then place cherries in the centers.

Pro tip: Pat pineapple rings dry with a paper towel to avoid a soggy cake!

Step 2: Mix & Pour the Batter

  1. In a bowl, combine the cake mix with eggs, oil, water, and vanilla (if using). Stir until smooth.
  2. Gently pour the batter over the pineapple layer. Use a spatula to spread it evenly.

Secret upgrade: Add 1/4 cup pineapple juice to the batter for extra tropical flavor!

Step 3: Bake to Perfection

  1. Preheat the oven to 350°F (175°C).
  2. Bake for 35-40 minutes. The cake is done when a toothpick comes out clean.

Watch closely: If the top browns too fast, tent it with foil.

Step 4: The Flip (Without Disaster)

  1. Let the cake cool in the pan for 10 minutes—no rushing!
  2. Place a large plate over the pan, grip tightly, and flip in one confident motion.
  3. Lift the pan slowly. If a pineapple sticks, gently nudge it with a knife.

5 Tips for the Best Pineapple Upside Down Cake

Tip 1: Avoid Soggy Bottoms
Always drain and pat pineapple rings dry. Excess moisture = gummy cake.
Tip 2: Boost Flavor with Brown Sugar
Dark brown sugar has more molasses, giving deeper caramel flavor than light sugar.
Tip 3: Don’t Skip the Cooling Step
Cooling lets the caramel set. Flip too soon, and the cake crumbles!
Tip 4: Add a Secret Ingredient
Stir 1 tbsp rum or extra pineapple juice into the batter for a flavor kick.
Tip 5: Serve It Warm
Microwave leftovers for 15 seconds to revive that gooey caramel magic.
Best Pineapple Upside Down Cake Recipe With Cake Mix (5 Tips!)

FAQs About Pineapple Upside Down Cake

Can I use fresh pineapple instead of canned?

Yes! Fresh pineapple works great. Just slice it thinly so it bakes evenly. Keep in mind that canned pineapple adds extra moisture and sweetness, so if using fresh, you may want to add 1–2 tablespoons of pineapple juice or milk to the batter.

Can I make pineapple upside down cake ahead of time?

Absolutely. You can bake it 1 day ahead. Let it cool completely, cover tightly, and keep at room temperature. For best texture, warm slices slightly before serving.

Do I need to flip the cake right out of the oven?

Yes. Let the cake cool for 5–10 minutes, then invert. Waiting too long can cause the caramelized sugar to harden and stick to the pan.

Why did my cake turn out dry?

A dry cake means it was baked too long or at too high a temperature.
Bake at 350°F (175°C) and check 5 minutes before the recommended time.

Can I freeze pineapple upside down cake?

Yes! Freeze individual slices or the whole cake:

  • Wrap tightly in plastic + foil
  • Freeze up to 3 months
    Thaw in the fridge overnight and warm before serving.

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