Pumpkin Cinnamon Roll Cookies

Cinnamon rolls and I kinda have a thing. You see, we’ve practically been lovers since the 3rd grade when I discovered they were the one thing the lunch ladies at my school made from scratch that actually tasted like food.

Chili and cinnamon roll days were a special occasion and only came around once every few weeks in the winter months. This meant every fourth Friday people went into an all-out flurry rushing to the cafeteria to claim their sticky prize. Little did they know I’d sidled them and was always first in line, wide-eyed gripping my tray with a silly grin on my face, waving my finger at the biggest cinnamon roll in the bunch chirping “Ooh ooh, mine mine,” at the lunch ladies. They surely hated my 10-year-old self, tragically crooked teeth and all.

What ensued next was practically material for “50 Shades of Grey.” As I sat perched on the brown plastic benches in our cafeteria I stole delicate bites of my cinnamon roll between sinfully large spoonfuls of chili and anticipated that last, ooey gooey center bite – a climax and tragic ending all in one. Once the experience drew to a close it was cold lunch city provided by mom until the next chili and cinnamon roll day came around.

I’ve tried to make cinnamon rolls from scratch before, but without my mom by my side gently instructing me at every tur they always turn out like hockey pucks – nowhere near worthy of being enveloped in creamy frosting and consumed while cuddled up in a cozy chair with a hot cup of tea. Not even close.

So my solution in the meantime? Cinnamon roll cookies. PUMPKIN cinnamon roll cookies. You know, because it’s fall and whatnot.

This caramel glaze is my mom’s super secret recipe that she would share with anyone who asks. I called her the night before I baked my cookies to copy down the instructions and once more when I was in the process of making it. I wanted to make sure it was just right; can’t bring cinnamon roll disgrace to the family name, after all.

Hmm, based on the texture, caramel flavor and how it practically slid off my whisk onto my cookies, I’d say I nailed it.

Wondering what they taste like? Imagine a delicate sugar cookie with a gooey pumpkin butter-brown sugar center and a melt-in-your mouth caramel glaze. One cookie in and you’ll already be dreaming about your next two.

These aren’t your delicate tea time, laugh with your mouth closed and legs crossed type of cookie. They’re more of a full fat chocolate milk from the can “eat like a trucker while grunting ‘yeeeee haw'” type of cookie. Get the picture? Yeah…good.

4.8 from 6 reviews
Pumpkin Cinnamon Roll Cookies
Prep time
Cook time
Total time
Delicate sugar cookies prepared in one bowl with a pumpkin butter-brown sugar center and topped with a rich caramel glaze.
Recipe type: Dessert
Serves: 24 cookies
  • 1 stick butter, slightly softened + 4 Tbsp for filling
  • 1/2 cup sugar
  • 1/2 cup brown sugar + 4 Tbsp for filling
  • 1 egg
  • 2 cups all purpose flour
  • 1 cup whole wheat pastry flour
  • 2 tsp baking powder
  • 1/2 cup milk
  • 1 tsp vanilla extract
  • 1/4 tsp salt
  • 1 tsp cinnamon
  • 4 Tbsp pumpkin butter
  • 1 tsp each cinnamon and pumpkin pie spice (for filling)
  1. Preheat oven to 375 degrees.
  2. Cream sugars and butter with mixer; add egg and beat until combined.
  3. Add dry ingredients to a sifter. Alternate adding milk and dry ingredients to the butter mixture while mixing. Then add vanilla and stir.
  4. Chill for 30 minutes before rolling out. Roll out into a rectangle on floured surface, spread with butter, pumpkin butter and top with brown sugar, cinnamon and pumpkin pie spice.
  5. Carefully and tightly roll into a log, then use floss or a serrated knife to cut into equally thin slices.
  6. Transfer to a baking sheet (they won't spread much) and bake for 14-15 minutes, being careful not to over-bake. They will be a little tender looking, but take them out, let them rest for 3-4 minutes on the baking sheet, and them transfer them to a cooling rack.
Nutrition Information
Serving size: 24 cookies; per cookie Calories: 145 Fat: 6 g Saturated fat: 3 g Carbohydrates: 20 g Sugar: 8.5 g Sodium: 71 mg Fiber: 1 g Protein: 2 g

4.8 from 6 reviews
Pumpkin Cinnamon Roll Cookie Glaze
Cook time
Total time
A rich 4-ingredient "caramel" glaze that comes together in minutes and tops these cookies (or actual cinnamon rolls) perfectly.
Recipe type: Dessert
Serves: 24 cookies
  • 4 Tbsp butter
  • 1/2 cup brown sugar
  • 2 cups powdered sugar
  • splash of milk
  1. Melt butter in a saucepan over medium-low heat.
  2. Add brown sugar and stir. Simmer the mixture while stirring frequently for 2-3 minutes.
  3. Remove from heat and add powdered sugar and milk and stir. If you desire a thicker or thinner frosting, compensate with more milk or powdered sugar.
  4. Spread or pour the glaze over the cookies (I used a spoon), sprinkle with more cinnamon or pumpkin pie spice (optional) and enjoy!
  5. Store in an air-tight container at room temperature to keep fresh for at least 3 days.
Nutrition Information
Serving size: 24 servings; per servgin Calories: 67 Fat: 1.9 g Sugar: 12 g

danaHi, I'm Dana! I am a food stylist, photographer, and author of the Food Photography School and the 31 Meals Cookbook.

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  1. says

    I love this! I’ve made plain ones (cinnamon roll sugar cookies) but I love your healthier pumpkin take here…and the caramel icing is just the icing on the … cookie. :)

  2. says

    I have the same thing for cinnamon rolls too, actually anything with cinnamon just feels so comforting somehow, especially in a chilly weather. its nearly getting warmer here where I live, but I’ll definitely give this recipe a go sometime. It just looks amazing!

  3. Lauren says

    these look GREAT! I’ve been looking for a yummy fall cookie to make. Just wondering, how did the texture turn out on these? are they crunchy? Chewy? Thanks!

    • Dana says

      Thanks Lauren! The texture was still soft, not really crunchy or chewy. More like a traditional soft sugar cookie with a gooey center and decadent glaze!

  4. Iris says

    I just made these and they taste AMAZING! The caramel icing really adds a whole new element (because duh, I tried a cookie straight out of the oven AND one with icing for a taste test). My only question is: how did you get yours shaped so well? For some reason I found my dough melted quickly enough so that despite a super floured surface it still stuck to my board and was really difficult to roll? Any suggestions?

  5. Nosizwe says

    Just made these coz they look yum. Substituted various things as can’t get pumpkin pie spice or pumpkin butter – not serious as I’ve made cinammon rolls before. Thought this would be an easier dough to work with. However, that’s not the case – the individual rolls have melded into one in the oven – the dough was too soft to start with I think. I’m sure they’ll taste good though.

    • Dana says

      Yes, the dough is soft but if you just throw it in the fridge for a few minutes before cutting them into individual cookies they should be fine. Hope they still turned out OK!

  6. Nosizwe says

    They are absolutely deiicious! Confession: I know why the dough is extra soft – my half cup measure wasn’t. It was a third cup measure – hahaha! That’s what comes of rushing! I used baked mashed pumpkin and preserved ginger with lots of cinammon and mixed spice. SOOOOO good! Thank you.

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