Loaded Cinnamon Roll/Cookie Cups


Yield: 8 Cinnamon Roll Cups


  • Pack of Pillsbury Cinnamon Rolls or cookie ingredients
  • Your choice of toppings! (Nutella, caramel, frosting, chocolate chips, marshmallow, peanut butter, fruits, fluff, etc.)


  • Muffin baking pan (any size will work depending on the size of the cups you want)

Let’s Make It!

  1. Take the cinnamon rolls out of the package and place one in each of the muffin tin cavities. For cookie cups, make the cookie dough and place cookie dough balls in the muffin cavities. If you’re using a small or large muffin pan, you may need to adjust accordingly.
  1. Bake as directed – when in doubt, bake a few minutes less to reduce the chance of burning.
  2. Take out of oven and immediately create a well in the middle of the rolls or cookies by using your hands or a utensil. These should resemble cup shapes.
Finished cinnamon rolls in a muffin baking pan.
I used a cooking spray lid to create the cookie cup wells!
  1. Let cool for 30 minutes in muffin tray.
  2. Fill ’em up!
  3. Store at room temperature, fridge, or freezer depending on toppings. Cinnamon roll and cookie cups by themselves will be fine at room temperature for a few days. If using the fridge, place a piece of bread or two in the same storage container with the cups to keep them from drying out.
  4. Try them after microwaving for a few seconds!

Notes & Alternatives

  • These are a great way to get rid of excess ingredients. Have some leftover frosting or toppings? Bake these cups and throw those leftovers in!
  • Placing bread with baked goods keeps them from drying out and getting hard.


  • It’s assumed cinnamon rolls were invented some time in Sweden.
  • Both April 10th and October 4th are said to be National Cinnamon Roll Day!
  • Cookies have been around for many hundreds of years and may have originated in 7th century Persia.
  • I thought of these after visiting Knead Donuts café in Providence, Rhode Island. In their front display case, a large, center collapsed cinnamon roll was out on display. It had looked like the middle collapsed in from the heavy frosting sitting on top for too long. But, this looked tasty, and I imagined myself biting into this large cinnamon cup and having the warm cream cheese ooze out. Being an idiot, I thought it was supposed to look like this and was excited to take a bite. Unfortunately, they served me a regular iced cinnamon roll! That evening, I decided to put this recipe to work!


Up close picture of a finished cinnamon roll cup filled with cream cheese, background is blurry several finished decorated cinnamon roll cups.
Birds eye view of several finished cinnamon roll cups with several fillings and decorations.

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