Caramelized Pineapple Cheesecake

This sweet Pineapple Upside-Down Cheesecake mashes up a rich, dreamy cheesecake and old-school pineapple upside-down cake. You'll bite into caramel-glazed pineapple and bright cherries sitting on top, then sink into creamy layers and soft cake. The pineapple slices look gorgeous when flipped out. Make this ahead so it's easier to slice and those flavors get even better.

INGREDIENTS

• Sour cream: Half a cup, makes the cheesecake extra creamy
• Eggs: 2 big ones, for structure in the cheesecake
• Pineapple juice: 1 tbsp, toss it into your cake mix if you want a little extra zing
• Yellow or strawberry cake mix: One box, for the cake (plus the things the box tells you to add)
• Butter: 1/4 cup, melted for the pineapple top layer
• Cream cheese: 16 ounces, let it soften up so mixing is easy
• Granulated sugar: 3/4 cup, sweetens the cheesecake
• Brown sugar: Half a cup, goes with the butter for caramelizing
• Pineapple slices: Canned or fresh, your pick for the fruity layer
• Maraschino cherries: These cheer up the top and add a pop of color
• Vanilla extract: One teaspoon, adds a cozy flavor boost

INSTRUCTIONS

Step 13:

Top it off with more maraschino cherries and a bit of whipped cream. Slice it up and dig in!

Step 12:

Turn your cheesecake upside down onto a plate so the pretty pineapple side faces up.

Step 11:

Stick the whole thing in the fridge for 4 hours or overnight. This helps everything set and makes serving way easier.

Step 10:

Once it’s out of the oven, give your cheesecake 10-15 minutes to cool. Slide a knife along the pan edge to loosen it up.

Step 9:

Bake everything together for about 50-60 minutes, or till the middle isn’t wobbly and the top looks golden.

Step 8:

Carefully pour your cake batter over the cheesecake mixture, making sure the layers stay put.

Step 7:

Now, mix the cake mix as the box says—you can splash in pineapple juice here if you want more of a tropical vibe.

Step 6:

Spoon the creamy cheesecake batter on top of that pineapple layer in your pan. Smooth it out gently.

Step 5:

Drop in the eggs one at a time, stirring after each. Now mix in the vanilla and sour cream so it’s super smooth.

Step 4:

Grab your cream cheese and beat it with sugar until it's nice and fluffy.

Step 3:

Lay the pineapple slices over the brown sugar layer, pop a cherry into every ring.

Step 2:

Pour that melted butter into your greased pan, sprinkle brown sugar on top. No need to be perfect.

Step 1:

Heat your oven up to 325°F (160°C) and grease up a springform pan well.

Serving and Storage Tips

• Bests served cold—chill it before you slice for the creamiest texture.
• Pop extras in a container with a lid and keep it in your fridge for up to three days.

Helpful Notes

• Want more pineapple punch? Add another tablespoon of the juice right to the cheesecake mixture.
• No cake mix? Make your own yellow cake batter if you’re feeling up for it.

Thoughts from Top Chefs

• Chef advise: letting your dessert chill overnight makes it hold together and taste way better!
• Chef advise: a splash of rum extract in your cake batter gives it that island feel.

The Magic of Pineapple Upside-Down Cheesecake

This dessert brings creamy cheesecake goodness and caramelized pineapple sweetness together in every single slice. Your friends will love it for birthdays or whenever you need a showstopper.

FAQs

Is it okay to use fresh pineapple?

Definitely—just slice it thin and dry it off with paper towels so things don’t get soggy.

How long does it need to chill?

At least four hours, but leaving it overnight makes it taste even better and cuts cleaner.

Can I add nuts on top?

Sure thing—throw chopped pecans or walnuts right on the brown sugar for crunch.

What can I swap for maraschino cherries?

Fresh or dried cherries work, or even candied pineapple pieces if you want.

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Summary

A sweet mix of creamy cheesecake and golden caramelized pineapple, this layered dessert is both eye-catching and irresistible. With fluffy cake and a buttery topping, it’s perfect for special days or sharing with loved ones. Chill it and serve for that fresh, tropical flavor!