Don’t be afraid! The first thing you need to know about baking your own sweet rolls is they are just as easy as 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! Like these Pineapple Upside Down Cake Sweet Rolls!
Can you believe you only need butter, sugar, eggs, and flour to start this recipe? You will begin making your sweet roll dough just like you do everyone’s favorite cookie dough, by creaming butter and sugar together, but before you do this, let’s activate your yeast so you don’t have to wait! Gently mix warm milk, 1 tablespoon of sugar, and 1 packet of yeast together with a fork. Set aside.
While your yeast is rising we can get started with the base of your dough. With your paddle or whisk attachment, cream your butter, granulated sugar, and brown sugar together until smooth. Add eggs, mixing between each addition. Incorporate 2 cups of flour into your creamed mixture 1/2 cup at a time.
Stop. What you have here is a basic cookie recipe! Now we are going to teach it to rise! Switch your mixer attachment to your dough hook. Pour in your yeast mixture. Top with the remaining 2 cups of flour. Start your mixer on the lowest setting. (Increase to the next setting if your mixer sounds like it needs more help.) Continue kneading dough for about 2 minutes. Transfer dough to a large lightly oiled bowl; cover with plastic wrap or a damp cloth. Allow your dough to rise for 1 hour in a warm place.
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.
Now that we’re flat, this is when most sweet roll recipes will have you spread butter across the dough, but because the pineapple is so moist already, I skip it. However, if you really love the butter flavor, add it anyway. It isn’t going to hurt your sweet roll at all.
Mix the cinnamon sugar. You have never had cinnamon sugar this good before — and may never make it with granulated sugar ever again after this! Promise! The combination of the brown sugar and cinnamon is really special. It adds another dimension of flavor to these sweet rolls. After you mix the two, go head and spread it evenly on your dough.
Drain your pineapple. Reserve the liquid to use it later when preparing your pineapple cream cheese frosting. Cover your dough with crushed pineapple, get your hands dirty and really mix it in with the cinnamon sugar a little too!
No pineapple upside down cake is complete without cherries; don’t go crazy with them though! I added pieces of maraschino cherries in all of the little bare spots that the pineapple didn’t cover. It was just enough to add a little extra something, but not so many that everyone thought it was a cherry sweet roll. If you don’t like cherries, you can omit them, but if you can live with them, they DO add both a visual and flavor elements to the sweet rolls that I think you will like.
Roll it up! We’re almost done! I know this sounds like a lot, but unless you are standing at the kitchen counter counting down the minutes, this is pretty effortless. I make a sweet roll every weekend and I never feel like it is a chore. Roll up your dough and cut them into 1/2-1 inch thick servings. Everyone will tell you to use floss for this, but honestly, if you don’t have any, you can cut them with a sharp knife or a steel scraper (that’s what I use!) If the roll goes a little flat from the cut, you can form the round shape with your hands before adding it to your pan.
Lightly grease two round pans and set your rolls into them, leaving space for your dough to rise a little more before baking. Allow to rest in a warm place for 30 minutes before baking. 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.
After about twenty minutes, remove the dough and water pan from the oven before preheating to 350 degrees.
Time to bake! I’m so excited you made it this far with me! The Pineapple Upside Down Cake Sweet Rolls are worth the effort we’ve put into them! You’ll see! Especially after you bite into those warm gooey cream cheese topped rolls! Eating them for breakfast feels a little like cheating. Is cake for breakfast allowed? I say yes!
While your beautiful rolls are baking, go ahead and prepare your pineapple cream cheese frosting. Don’t skip this step. This frosting is amazing and if you have a food processor, smoothie blender, or you already cleaned your mixer, it’s a dump it and go thing! I use a NutriBullet and all I do is 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. It seems like such a waste after you watch your NutriBullet do it’s thing!
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. After that, immediately top your Pineapple Upside Down Cake Sweet Rolls with your Pineapple Cream Cheese frosting and dig in! If you’re feeling like you really deserve a reward, go straight for the center roll — that’s the best one!
Pineapple Upside Down Cake Sweet Rolls
- 1 cup Warm Milk
- 1 tbsp Sugar
- 1 packet Yeast
- 1/2 cup Butter
- 1/2 cup Granulated Sugar
- 1/4 cup Brown Sugar
- 2 Eggs
- 4 cups All Purpose Flour
- 1 cup Brown Sugar
- 3 tbsp Ground Cinnamon
- 1 20 oz can Crushed Pineapple
- 5-10 Maraschino Cherries, sliced
- 1/4 cup Butter
- 1/2 cup Cream Cheese
- 3 tbsp Pineapple Juice/Heavy Syrup
- 1 cup Powdered Sugar
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.