Crumbl Pumpkin Cinnamon Roll Cheesecake Cookies

Steps

1. 1Cheesecake filling / frosting: Add the cream cheese and sugar to a bowl. Whisk on medium-high speed for 1-2 minutes until the mixture is creamy, scraping the bowl along the way
2. 2Add the cold heavy cream and vanilla. Whisk for another 1-2 minutes, or until the mixture becomes thick and fluffy and reaches the medium peak stage (i.e., starts to hold shape). Do not overmix
3. 3Line a small tray with parchment paper. Use a cookie scoop to scoop 6 balls of the cheesecake mixture onto the tray, each weighing ~30g. Transfer this tray to the freezer to allow the cheesecake filling to firm up
4. 4Transfer the remaining cheesecake mixture to a piping bag with a round tip. This will become your cream cheese icing. Keep in the fridge for use at the end
5. 5Cinnamon roll swirl: Add the brown sugar, butter, flour, cinnamon and salt to a bowl. Whisk for 1 minute until the ingredients are combined (it will be a grainy mixture, don't worry)
6. 6Place parchment paper on a small baking sheet. Spread the cinnamon mixture on it so it is about 1/2 cm in thickness. Then transfer to the freezer
7. 7Pumpkin snickerdoodle cookie dough: Start by drying the pumpkin puree if you haven't already. Spread it thinly on a large plate, and press paper towels on top to absorb water. Once the paper towels are soaked, replace them with new ones and stir and respread the puree. Keep repeating until the paper towels don't get wet easily (about 4 times) and the puree is half of its original volume*
8. 8Add the butter, brown sugar and granulated sugar to a bowl and whisk on medium high speed for 2-3 minutes until the mixture turns fluffy and light in color. Keep scraping the bowl along the way
9. 9Add the egg, egg yolk and vanilla. Whisk for another minute until a creamy mixture forms
10. 10Add the dried pumpkin puree, and whisk until just combined
11. 11Now sift the flour, pumpkin spice, baking powder, baking soda and salt in a separate bowl and mix to combine. Add the dry ingredients to the cookie dough in 2 additions, and use a rubber spatula to gently fold until the flour is just combined. Take care not to overmix
12. 12If the dough feels too soft and sticky, refrigerate it for 10-15 minutes until it reaches a firmer consistency that's easier to shape
13. 13Cinnamon sugar coating: Mix the cinnamon and sugar in a bowl
14. 14Assembly: Once all components are ready, it's time to assemble the cookie balls. Remove the cinnamon roll swirl from the freezer. It should be a solid bark. Break it into chunks (roughly ~1/2" to 1" big). Add half of the chunks on top of the cookie dough and gently fold them in. Then add the other half and gently fold again. Try to spread them evenly in the cookie dough while still keeping them intact (i.e., you don't want them to melt and mix into the cookie dough)
15. 15Now remove the cheesecake scoops from the freezer, too
16. 16Divide the cookie dough into 6 5oz portions (you may have a small bit left over). Working one piece a time, gently flatten in the palm of your hand and place a cheesecake scoop on top. Then fold over the cookie dough to completely encase the cheesecake scoop, and shape into a ball
17. 17Repeat with all 6 portions of cookie dough
18. 18One by one, roll each cookie dough ball in the cinnamon sugar mixture to coat it on all sides
19. 19Place the cookie dough balls on a plate or tray lined with parchment paper, and refrigerate overnight (minimum of 6 hours)
20. 20Baking & decoration: When you're ready to bake after chilling, pre-heat the oven to 375F (conventional / no fan) and line a large light colored baking sheet with parchment paper
21. 21Place the chilled cookie dough balls on the baking sheet, keeping at least 3" between each
22. 22Place in the oven and bake at 375F for 5 minutes, then drop the temperature to 340F and bake for another 14-15 minutes for a total baking time of 19-20 minutes. The cookies are done baking when they are golden in color, look set on the edges but are still soft to touch in the middle (this is because of the cheesecake filling).
23. 23Remove from the oven and let cool at room temperature for 1 hour
24. 24Once the cookies are cool, pipe on swirls of cream cheese frosting (reserved from the previous day)
25. 25Serve and enjoy!