Table of Contents
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Why This Recipe Works
The beauty of this recipe lies in its simplicity. You’re essentially taking pre-made cinnamon roll dough and elevating it with fresh pineapple and maraschino cherries. The warm, caramelized pineapple adds a juicy sweetness that pairs perfectly with the soft, gooey cinnamon rolls. Plus, the cinnamon sugar coating gives everything an extra layer of flavor that’s just delightful. Trust me, this is where it really comes together.
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Ingredients
Here’s what you’ll need to get started:
- Pillsbury Cinnamon Roll Dough (with icing)
- Pineapple Rings (1 per waffle)
- Maraschino Cherries (1 per waffle)
- 2 tablespoon Brown Sugar
- 2 teaspoon Ground Cinnamon
- 1 teaspoon Nutmeg
- Powdered Sugar (optional, for dusting)

Fresh pineapple works here, but I found that the canned pineapple rings are the perfect size for this. They fit perfectly underneath the cinnamon roll, and hold together well while cooking.

How to Make It
Let’s dive into the cooking part. Grab a small bowl and mix the brown sugar, ground cinnamon, and nutmeg together. You really want to make sure it’s well combined because this is what gives your pineapple that delicious cinnamon sugar crust.

Next, take each pineapple ring and coat it thoroughly in that cinnamon sugar mixture. Don’t be shy with it - this is where the flavor really starts to shine.
Now, preheat your waffle iron. I like to give it a light greasing with cooking spray or a little oil to prevent sticking. When it’s nice and hot, place a coated pineapple ring on the waffle iron. Pop a maraschino cherry right in the center of that ring. It adds a nice pop of color and sweetness!

Then you’ll take a cinnamon roll from the package, place it right on top of the pineapple, and close the lid. You want to cook it for about 3-4 minutes. Keep an eye on it; waffle irons can vary in heat, and you don’t want to burn your creation. You’re looking for that golden brown color, and trust me, the aroma wafting through the kitchen is going to be hard to resist.

Once they’re done, carefully remove them from the waffle iron. I like to let them cool for a minute because that cinnamon roll filling can be super hot. Drizzle the icing from the cinnamon roll package over the top while it’s still warm, and if you’re feeling fancy, dust a little powdered sugar on top too if you'd like.
Tips and Variations
If you want to get a little adventurous, you could add some chopped nuts for a nice crunch or even a sprinkle of coconut for that tropical vibe. Not a fan of maraschino cherries? Swap them out for fresh berries instead. The beauty of this recipe is its flexibility, so feel free to experiment a bit.

Also, if you’re serving a larger crowd, consider making these in batches. You can keep them warm in a low oven while you finish cooking the rest.
Serving Ideas
These Pineapple Upside Down Cinnamon Waffles are great on their own, but you could definitely serve them alongside some crispy bacon or sausage for a complete breakfast spread. A side of fresh fruit wouldn’t hurt either. If you want to kick it up a notch, serve them with a scoop of vanilla ice cream for dessert. I mean, who doesn’t love dessert for breakfast?
Watch Me Make It
Closing
So there you have it! Pineapple Upside Down Cinnamon Waffles - a fun and delicious way to switch up your breakfast routine. They’re easy to make, bursting with flavor, and absolutely perfect for sharing. Give it a shot and enjoy the delightful combination of flavors; I guarantee it’ll become a favorite in your household, just like it did in mine!
Frequently Asked Questions
Can I make the Pineapple Upside Down Cinnamon Waffles ahead of time?
Yes, you can prepare the pineapple and cherries on top of the cinnamon rolls ahead of time and store them in the refrigerator. Assemble and bake the waffles just before serving for the best texture.
How should I store leftover Pineapple Upside Down Cinnamon Waffles?
Store leftover waffles in an airtight container in the refrigerator for up to 3 days. You can also freeze them for longer storage.
What is the best way to reheat these waffles?
To reheat, place the waffles in a toaster oven or conventional oven at 350F for about 5-7 minutes or until warmed through. You can also use a microwave for about 30-60 seconds, but the texture may not be as crisp.
Can I substitute the Pillsbury Cinnamon Roll Dough with another type of dough?
Yes, you can use other types of dough, such as homemade cinnamon roll dough or even pancake batter, though the texture may vary.
What can I use if I donu2019t have maraschino cherries?
If you don't have maraschino cherries, you can substitute them with fresh cherries, strawberries, or other fruits like blueberries or raspberries for a different flavor.
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Ingredients
- Pillsbury Cinnamon Roll Dough (with icing)
- Pineapple Rings (1 per waffle)
- Maraschino Cherries (1 per waffle)
- 2 tablespoon Brown Sugar
- 2 teaspoon Ground Cinnamon
- 1 teaspoon Nutmeg
- Powdered Sugar (optional)
Instructions
- In a small bowl, mix the brown sugar, cinnamon, and nutmeg.
- Coat each pineapple ring thoroughly in the cinnamon sugar mixture.
- Heat and lightly grease your waffle iron.
- Place a coated pineapple ring on the waffle iron, add a maraschino cherry in the center, and top with a cinnamon roll.
- Close the waffle iron and cook for about 3-4 minutes until golden and cooked through.
- Remove carefully, let cool slightly, drizzle with the cinnamon roll icing, and dust with powdered sugar if desired.















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