Step 1

Brown the Butter: See note below if skipping this step. Add butter to a medium saucepan over medium heat. Melt the butter, stirring occasionally. Once it's melted, turn the heat to medium-low, and continue cooking the butter, stirring frequently. The butter will get foamy and bubbly, then turn a deep golden shade with a nutty, caramely aroma. (This will take about 4-6 minutes once the butter has melted.) Pour into a large bowl, making sure to scrape in all the brown bits from the bottom of the pan, and allow to cool in a heat-safe bowl for 40 to 45 minutes in the freezer. The butter must be room temperature, not hot before you use it, but it will still be in a liquid state. Tip: If you left the butter in the freezer too long and it solidified, just microwave it gently to get it back to a liquid, but make sure it isn't hot.

Step 2

Make Snickerdoodle Dough: Add the cooled brown butter to a large bowl. Whisk in the sugars. Add the eggs and vanilla, and whisk until smooth and combined, about 30-45 seconds. Fold in the dry ingredients, until completely incorporated into a dough. If it's a bit crumbly, just keep mixing - it'll come together. Or, use your mixer to get everything combined quickly at the end. Scrape the sides and bottom of the bowl to check for any dry bits that didn't get mixed in. Cover the dough with a clean kitchen towel or plastic wrap and pop in the fridge to rest while you make the filling.

Step 3

Make Cinnamon Roll Filling: In a small bowl, cream together all the cinnamon roll filling ingredients. If it's particularly warm in your kitchen, pop this in the fridge so it doesn't get melty while you make the cookie dough. Make Cinnamon Sugar for Rolling: In a small bowl, stir together the cinnamon and sugar for rolling.

Step 4

Assemble & Chill: Scoop cookie dough balls that are 65 grams in size (about 3.5 tablespoons). Flatten each dough ball and add 2 tsp of cinnamon roll filling to the center. Encase the filling in the dough completely, making sure any seams are smoothed shut, and roll the dough back into a ball. Roll in the cinnamon sugar before chilling, so it adheres better. Chill the dough balls for at least 30 minutes in the freezer or at least 3 hours in the fridge. They should feel solid coming out of the freezer. If they aren't, freeze them longer. See note below if you want to make smaller cookies & stretch the yield.

Step 5

Bake: Preheat your oven to 365℉. Line a few baking sheets with parchment paper. Place 5-6 cookies on a cookie sheet, allowing space between for them to spread. Bake one sheet at a time (keeping excess cookie dough balls in the fridge/freezer to stay cold). Bake for 10-13 minutes. The edges of the cookies will appear set and the tops will look just done. Place a round cutter around the outside of the cookies to "scoot" or swirl them into a perfect circle - this helps them look a bit thicker as well. (Just don't actually cut off any wonky edges with the cutter!)Place cookie sheet on a wire rack to cool while you make the glaze.

Step 6

Make Glaze: Whisk together all glaze ingredients and drizzle over the warm cookies once they've been out of the oven about 15 minutes.

Step 7

Serve + Store: Enjoy cookies warm (they need to cool for about 20-30 minutes) or at room temperature! Store cooled cookies in an airtight container at room temperature for 4-5 days or in the fridge for 6-7.

Step 8

Make-Ahead Tips: The stuffed cookie dough balls can be made & stored in an airtight container in the fridge for 1-2 days before baking. Or, it can be frozen for 1-2 months. Freeze dough balls in a single layer on a lined baking sheet, then transfer to a freezer bag once frozen so the balls don't all stick together. Bake from frozen, adding 1-2 minutes to the bake time as needed.