I know sweet rolls can be a bit intimidating, especially when they come with a name like Pineapple Upside Down Sweet Roll recipe. Please don’t be afraid! The first thing you need to know about baking your own sweet rolls is they are just as easy as baking cookies.

For years I avoided making cinnamon rolls on my own because I didn’t know how easy they were. I didn’t realize that at the heart of every great sweet roll recipe was the basic cookie dough. Once I learned they were just cookies that learned to rise, I couldn’t be stopped! Now I create creative sweet rolls from almost any cookie or cake I can think of!

To make Pineapple Upside Down Sweet Rolls you will need the following supplies: milk, sugar, active dry yeast, butter, granulated sugar, brown sugar, eggs, all purpose flour, ground cinnamon, crushed pineapple, maraschino cherries, butter, cream cheese, pineapple juice, & powdered sugar.

Table of Contents

Tips & tricks to making Pineapple Upside Down Sweet Rolls

I’ve made plenty of sweet rolls by hand in my day but I’m not going to lie a stand mixer makes the job much easier!

Always start with your mixer on the lowest setting and work your way up if it sounds like it needs a bit of help. This is suggested for your mixer and it helps keep things from flinging everywhere!

You can easily let your dough rise in the refrigerator. I prefer to do it after the kneading but in all honestly it’s usually after they have been shaped. This allows me to make the sweet rolls the night before and I only have to bake them in the morning. TIME SAVER!

Before rolling your dough out, form dough into a log horizontally in front of you. I feel like this makes rolling my dough into the perfect rectangle a million times easier.

Skip the butter when you’re layering your pineapple and sugar on your sweet dough this time. The pineapple provides enough juice to help your sugars dissolve.

When you drain your pineapple reserve the juice for your icing.

You can certainly omit the cherries but they add such a wonderful pop of color why would you?!

We’ve all heard that unflavored floss works the best to cut your sweet roll dough and I can’t argue with that, however, a steel scraper or sharp knife is what I use.

If your kitchen is still a little cool, rise rolls in a warm oven. Anything under 200 degrees is ideal. To keep them from drying out before baking, add a pan of warm water to the bottom of your oven. Remove the pan of water before baking.

A NutriBullet makes quick work of the icing. Toss in the cream cheese, butter, powdered sugar, and splash of pineapple juice and turn it on for a minute or two. It’s so easy it’s almost laughable that I’ve ever bought cream cheese frosting before.

When your timer goes off on the oven, check your rolls by gently pressing on the center sweet roll. If the roll bounces back up, or seems a firm, they are done. If it sinks, bake them for about five more minutes.

Pineapple Upside Down Sweet Roll Recipe FAQS

Here are some of the most frequently asked questions about making sweet rolls:

Can you put dough in the fridge after it has risen?

You certainly can! It’s best to refrigerate your dough after the kneading process. Place your dough in a lightly greased or oiled bowl and cover the dough tightly with saran wrap. When you’re ready to use your dough punch it down and give it a couple minutes of rest time. Once the dough has rested you can shape and use it as per the recipe.

You can refrigerate your dough after it’s been shaped as well for its last rise. I do this often as I want to make the rolls at night and not have to fuss with them in the morning. I make my rolls up until the baking step and will let them rise covered loosely in a greased pan overnight. Then I bake them according to the directions first thing in the morning, remembering to allow an extra minute or two since the dough will be cold.

What is a sweet dough?

A basic sweet dough is one that is perfect for many reasons including sweet dinner rolls, cinnamon rolls, and even crescent rolls. Generally sweetened with sugar it becomes the base of many recipes, most notably cinnamon or sweet rolls.

How do you roll out dough?

Prep your workspace and rolling pin with a generous dusting of flour. Before rolling your dough out, form dough into a log horizontally in front of you. I feel like this makes rolling my dough into the perfect rectangle a million times easier. Use your hands to press out the dough into the start of a rectangle.

With your rolling pin continue to roll your dough out with an even amount of pressure, keeping your rectangle shape. You will need to turn your dough several times throughout the process to ensure that you don’t have any sticking.

HELPFUL TOOLS TO MAKE PINEAPPLE UPSIDE DOWN SWEET ROLLS

The following are affiliate links. We are a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for us to earn fees by linking to Amazon.com and affiliated sites. This doesn’t cost you any more money, but helps me keep the blog live!

First on the list is my Kitchen Aid Stand Mixer. It’s truly a workhorse and is so versatile! From mashing potatoes to shredding chicken, whipping up your favorite cake or you favorite homemade whip cream, a stand mixer can do the job.

As I mentioned above a NutriBullet works wonder to whip up the icing quickly! It’s also a champ at keeping up with the demands of a morning smoothie.

Pineapple Upside Down Sweet Roll Recipe

Sunday breakfast just got better with these absolutely divine cinnamon rolls that replicate your favorite pineapple upside down cake. Much like your favorite cookie recipe these cinnamon rolls start with creaming your butter and sugar together. The addition of yeast doesn’t have to make them something to be scared of!

If you love these pineapple upside down sweet rolls as much as we do please don’t forget to rate them 5 stars!

Pineapple Upside Down Cake Cinnamon Roll Recipe

Ingredients

Roll Ingredients

1 cup Warm Milk
1 tbsp Sugar
1/2 cup Granulated Sugar
1 packet Yeast
1/2 cup Butter
1/4 cup Brown Sugar
2 Eggs
4 cups All Purpose Flour

Filling Ingredients

1 cup Brown Sugar
3 tbsp Ground Cinnamon
1 20 oz can Crushed Pineapple
5-10 Maraschino Cherries, sliced

Frosting Ingredients

1/4 cup Butter
1/2 cup Cream Cheese
3 tbsp Pineapple Juice/Heavy Syrup
1 cup Powdered Sugar

Instructions

Combine warm milk, 1 tbsp granulated sugar, and yeast in a small bowl. Set aside.
Cream butter, sugar, brown sugar, and eggs with your mixer using the paddle attachment. Slowly mix in 2 cups of flour.
Switch to your dough hook attachment. Pour in the yeast mixture all at once. Add remaining 2 cups of flour. Knead dough on a 1-2 speed setting until the flour is fully incorporated (about 3 minutes).
Transfer dough into a lightly oiled large bowl. Cover with plastic wrap and allow to rise in a warm place for 1 hour.
Prepare filling before rolling dough.
Slice cherries. Drain pineapple, reserve liquid, set aside.
Mix Brown Sugar and Cinnamon together, set aside.
After dough has risen for 1 hour, roll dough on a floured surface into a large rectangle. Top with pineapple and cinnamon sugar mixture. Add cherry slices randomly.
From the long side, roll your dough tightly.
Starting at the middle, cut dough log into 1 inch thick rolls with a dough scraper or floss.
Lightly grease two round pans. Divide your rolls in half, place half in each dish. Allow to rest in a warm place for 30 minutes before baking.
Heat oven to 350 degrees.
Bake rolls for 25-30 minutes.
Prepare your pineapple cream cheese frosting by combining butter, cream cheese, pineapple juice/syrup, and powered sugar. Mix until smooth. Set aside.
Once the rolls are baked, top each with frosting. Serve warm.