Pillow Soft Cinnamon Rolls

Featured in: Weekend Farmhouse-Style Treats

Create beautifully soft, pillowy cinnamon rolls using a simple yeast dough enriched with milk, butter, and eggs. Roll the dough thin, spread with softened butter, then generously coat with a brown sugar and cinnamon mixture. Slice into twelve portions and arrange in a baking dish for the second rise. Bake until golden, then top with homemade cream cheese glaze while still warm for maximum decadence and flavor.

Updated on Fri, 16 Jan 2026 16:46:00 GMT
Freshly baked Pillow Soft Cinnamon Rolls on a rustic wooden board, showcasing their fluffy texture and generous cream cheese glaze. Pin This
Freshly baked Pillow Soft Cinnamon Rolls on a rustic wooden board, showcasing their fluffy texture and generous cream cheese glaze. | orchardflint.com

The morning sunlight streamed through my kitchen window as I pulled these cinnamon rolls from the oven for the first time. The aroma filled every corner of my home, drawing my family to the kitchen before I could even call them. Watching their faces as they took that first bite - eyes closed, shoulders relaxing - I knew this recipe would become our weekend tradition. Something magical happens when butter, cinnamon, and sugar transform ordinary dough into pillowy swirls of comfort.

Last Christmas morning, I woke at dawn to prepare these for my visiting in-laws. My father-in-law, usually stoic and reserved, wandered into the kitchen following the cinnamon trail. He stood beside me, coffee in hand, and shared stories of his grandmother making similar rolls during his childhood. In that moment, these simple rolls bridged generations and created a connection I hadnt expected.

Ingredients

  • Active Dry Yeast: Always check the expiration date - I once spent hours wondering why my dough wouldnt rise only to discover my yeast had expired months earlier.
  • Warm Milk: The perfect temperature feels like warm bath water on your wrist - too hot will kill the yeast, too cool and it wont activate properly.
  • Unsalted Butter: Using unsalted lets you control the exact saltiness of your rolls, but Ive used salted in a pinch by reducing the added salt.
  • Ground Cinnamon: Freshly ground makes a noticeable difference - I keep cinnamon sticks on hand and grind them in small batches for the most vibrant flavor.
  • Cream Cheese: Full-fat creates that perfect tangy-sweet balance in the glaze, though reduced-fat works if thats what you have on hand.

Instructions

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Wake Your Yeast:
Pour warm milk over your yeast with a spoonful of sugar and watch for tiny bubbles forming on the surface. This frothy reaction is your first clue that greatness is coming.
Create Your Dough:
Mix in your remaining ingredients until the dough pulls away from the bowl sides. It should feel slightly tacky but not sticky enough to coat your fingers.
First Rise Magic:
Place your dough ball in a greased bowl and cover with a damp cloth. The transformation during this hour of rising still amazes me every time.
Roll With Purpose:
Press the dough into a rectangle, taking your time to make it even. Those few extra moments of careful shaping make all the difference in how uniformly your rolls bake.
Fill With Generosity:
Spread that butter all the way to the edges before sprinkling your cinnamon-sugar mixture. I run my fingers along the far edge to leave a clean strip for sealing the roll.
Roll and Slice:
Roll the dough tightly from the long edge, using your fingertips to maintain even pressure. For perfect slices, I use unflavored dental floss slipped under the log and crossed over the top.
Second Rise Patience:
Arrange your spirals in the baking dish with a finger-width space between them. Theyll grow to touch during the second rise, creating that perfect pull-apart texture.
Golden Perfection:
Bake until the tops turn amber and your kitchen smells like heaven. If they brown too quickly, tent with foil to protect while the centers finish cooking.
Glaze While Warm:
The still-warm rolls will allow some glaze to melt into the crevices while leaving enough creaminess on top. I always make extra glaze because someone inevitably wants more.
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Cook complete meals by frying, sautéing, simmering, and boiling with easy nonstick cleanup every day.
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Warm Pillow Soft Cinnamon Rolls arranged in a baking dish, with a gooey cinnamon-sugar swirl visible in each golden-brown roll. Pin This
Warm Pillow Soft Cinnamon Rolls arranged in a baking dish, with a gooey cinnamon-sugar swirl visible in each golden-brown roll. | orchardflint.com

On a particularly difficult Monday, when everything seemed to go wrong, I pulled a batch of these rolls from the freezer and reheated them for an impromptu family breakfast. As we gathered around the table, the stress melted away with each shared bite and laugh. My daughter dubbed them our official comfort food, and now we make them whenever someone needs a bit of edible reassurance.

Make-Ahead Magic

One Sunday evening, with Monday looming, I decided to experiment with overnight preparation. After shaping the rolls and placing them in the baking dish, I covered them tightly and refrigerated overnight instead of doing the second rise. The next morning, I let them come to room temperature for about an hour while the oven preheated. The result was actually better than my standard method - the slow, cold rise developed a deeper flavor complexity that had everyone asking what Id changed.

Troubleshooting Tips

The winter my furnace broke, my dough refused to rise in my chilly kitchen. After that disaster, I learned to create a proofing box by placing the covered dough in an oven with just the light turned on. The gentle heat from the bulb creates the perfect environment when your kitchen is too cold. For summer baking when my kitchen runs hot, I find the dough can over-rise quickly, so I check it frequently and sometimes use cooler milk to slow things down.

Variations Worth Trying

During apple season, I often add finely diced apples to the filling, creating pockets of juicy sweetness that complement the cinnamon perfectly. For holiday gatherings, a sprinkle of orange zest in the dough and a tablespoon of orange juice in the glaze transforms these rolls into something festive and bright. Last Thanksgiving, I added chopped pecans and a touch of maple extract to both the filling and glaze, which earned me more compliments than the turkey.

  • For a twist with depth, try brown butter in the glaze instead of regular butter - the nutty notes are absolutely worth the extra few minutes.
  • Adding cardamom alongside the cinnamon creates a subtle chai-inspired flavor that pairs beautifully with afternoon tea.
  • When serving to chocolate lovers, sprinkle mini chocolate chips over the cinnamon-sugar layer before rolling for melty pockets of chocolate surprise.
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A close-up view of Pillow Soft Cinnamon Rolls drizzled with rich vanilla glaze, perfect for a cozy weekend breakfast or brunch. Pin This
A close-up view of Pillow Soft Cinnamon Rolls drizzled with rich vanilla glaze, perfect for a cozy weekend breakfast or brunch. | orchardflint.com

These cinnamon rolls have become more than just a recipe in my collection - theyve become the centerpiece of countless family moments and the requested birthday breakfast year after year. I hope they bring as much joy to your kitchen as theyve brought to mine.

Recipe FAQs

Why is my dough not rising properly?

Ensure your yeast is fresh and active by checking the expiration date. The warm milk should be between 105-110°F (40-43°C)—too hot kills yeast, too cold slows fermentation. Keep dough in a draft-free, warm location for optimal rising.

Can I make these rolls ahead of time?

Yes! Shape the rolls and place them in the baking dish, cover tightly, and refrigerate overnight. Remove from the refrigerator and allow them to rise at room temperature for about one hour before baking.

How do I prevent the rolls from drying out?

Keep the dough covered during rising with a damp towel or plastic wrap. Don't overbake—remove from the oven when golden brown. Apply glaze while rolls are still warm to keep them moist and tender.

What's the best way to slice the rolls?

Use a sharp serrated knife dipped in warm water, wiping clean between cuts. Alternatively, unflavored dental floss works wonderfully—slide it under the roll and cross the ends above, pulling tightly downward for clean, even slices.

Can I customize the filling?

Absolutely! Add chopped pecans, walnuts, or raisins to the cinnamon-sugar mixture. For variations, try cardamom, nutmeg, or a hint of orange zest mixed with the brown sugar and cinnamon.

How should I store leftover rolls?

Store covered at room temperature for up to two days, or refrigerate for up to one week. Reheat gently in a 300°F (150°C) oven for 10-15 minutes, or microwave individual rolls for 20-30 seconds until warm.

Pillow Soft Cinnamon Rolls

Indulgently fluffy cinnamon rolls with buttery swirls, brown sugar-cinnamon filling, and creamy glaze—ideal for weekend mornings.

Time to Prep
30 minutes
Time to Cook
25 minutes
Overall Time
55 minutes
Created by Luke Campbell


Skill Level Medium

Cuisine Type American

Makes 12 Portions

Dietary Details Suitable for Vegetarians

What You’ll Need

Dough

01 4 cups all-purpose flour
02 2 1/4 tsp active dry yeast (1 packet)
03 1 cup warm milk (about 110°F)
04 1/3 cup granulated sugar
05 1/3 cup unsalted butter, melted
06 2 large eggs, room temperature
07 1 tsp salt

Filling

01 2/3 cup packed light brown sugar
02 2 1/2 tbsp ground cinnamon
03 1/4 cup unsalted butter, very soft

Cream Cheese Glaze

01 4 oz cream cheese, softened
02 1/4 cup unsalted butter, softened
03 1 cup powdered sugar, sifted
04 1/2 tsp vanilla extract
05 2-3 tbsp milk

Step-by-Step Guide

Step 01

Activate Yeast: In a large bowl, dissolve yeast in warm milk with 1 tbsp sugar. Let stand until frothy, about 5-7 minutes.

Step 02

Mix Wet Ingredients: Add remaining sugar, melted butter, eggs, and salt. Mix until combined. Gradually add flour, mixing until a soft dough forms.

Step 03

Knead and First Rise: Knead dough on a floured surface for 6-8 minutes, or until smooth and elastic. Place in a greased bowl, cover, and let rise in a warm place until doubled, about 1 hour.

Step 04

Roll Dough: Punch down dough and turn onto a lightly floured surface. Roll into a 16x12-inch rectangle.

Step 05

Add Filling: Spread soft butter for filling evenly over dough. Sprinkle with brown sugar and cinnamon mixture.

Step 06

Form Rolls: Starting from a long edge, tightly roll up the dough. Pinch seam to seal. Cut into 12 equal rolls.

Step 07

Second Rise: Place rolls in a greased 9x13-inch baking dish. Cover and let rise until nearly doubled, about 35-45 minutes.

Step 08

Bake: Preheat oven to 350°F. Bake for 22-25 minutes, until golden brown.

Step 09

Prepare Glaze: While rolls bake, beat together cream cheese, butter, powdered sugar, vanilla, and enough milk for a spreadable glaze.

Step 10

Finish and Serve: Let rolls cool for 10 minutes, then spread glaze over warm rolls. Serve immediately.

Needed Gear

  • Large mixing bowls
  • Stand mixer with dough hook (optional)
  • Rolling pin
  • 9x13-inch baking dish
  • Sharp knife or dental floss (for slicing rolls)
  • Measuring cups and spoons

Allergy Advisory

Review all ingredients for allergens. Check with a health expert if you have concerns.
  • Contains wheat (gluten), eggs, milk, and dairy products.
  • Those with allergies should check all labels for cross-contamination.

Nutrition Details (per portion)

This data is provided for your reference. Always consult with a healthcare professional for nutrition advice.
  • Caloric Value: 345
  • Fats: 13 grams
  • Carbohydrates: 51 grams
  • Proteins: 6 grams