With a hand mixer or a stand mixer fitted with the paddle attachment, beat together the butter and brown sugar until the mixture is light and fluffy (2-3 min.)
Beat in the egg and vanilla until well combined.
Add in the flour, baking powder, cinnamon and salt. Use a rubber spatula to fold the ingredients together just until no flour streaks remain.
Cover the dough and leave it in the fridge to chill for at least 30 minutes, or for up to 2 days.**
Preheat the oven to 350°F / 175°C. Line a cookie sheet with parchment paper or with a silicone baking mat.
Use a 3 tbsp. cookie scoop to dish out the cookies onto the prepared cookie sheet. Evenly space the cookies apart to allow room for spreading. Bake for 10-12 minutes, until the sides of the cookies start to turn golden brown.
Immediately after taking the cookies out of the oven, take a bowl that is slightly larger than the cookies and swirl it around over the cookies to make them a little more uniform and circular.
Cheesecake Frosting
In a small bowl, beat together the cream cheese, butter and salt until smooth.
Add in the powdered sugar and mix until the mixture is smooth and free of lumps. Then, mix in the vanilla.
Wait for the cookies to cool down to room temperature before frosting. Generously frost each cookie with the cheesecake frosting, then top each cookie with 1 tbsp. of apple pie filling. Enjoy!
Notes
Affiliate links: Kitchen Scale (my favorite) | Kitchen scale (great starter option) | | Oven Thermometer | Cookie Scoops | Cookie Sheet Pan | Milk Pan |*You can use store-bought filling or make your own! I have a recipe for apple pie filling linked above. This recipe makes *way* more than you'll need for the cookies, so you can scale it down or keep the extras stored in the freezer!**You can make the dough and keep it stored in an airtight container in the fridge for up to 2 days before baking it. Just be sure to bring the dough out to sit at room temperature for a little bit, until it becomes soft enough to scoop again. For longer term storage, scoop out the dough balls and freeze them on a baking sheet or tray. Once they're completely frozen, you can transfer them to a ziploc or airtight container and keep them frozen for up to 1 month. I'd recommend letting the dough sit out for 20 min. before baking it, or thawing it in the fridge overnight before baking it. Please note that your cookies will likely bake up a little thicker.Store extra frosted cookies in an airtight container in the fridge.