Preheat oven to 350°F, and line cupcake pans with cupcake liners. Set aside.
In a large bowl, whisk together the flour, baking powder, baking soda, salt, and cinnamon until combined. Set aside.
In a medium bowl or stand mixer, whisk the brown sugar and eggs together until combined. Whisk in the pumpkin, butter, milk, and vanilla until well mixed.
Pour the wet ingredients into the dry ingredients and stir until just combined. Do not overmix the batter.
Transfer batter into prepared pans, filling about ½- 2/3 full. (I like to use a large cookie scoop for this part). Bake for 15-18 minutes or until a toothpick inserted in the center comes out clean. Allow to cool completely before filling or frosting.
Quick note on caramel sauce -
Caramel sauce can be purchased at any grocery store, or this Salted Caramel Sauce from Smuckers is thicker than most that I've found and works best for a cupcake drizzle!
If you want to make your own caramel sauce, my favorite recipe is this one from AverieCooks. No caramel recipe is fool-proof, but this one gave me the least trouble with burning and crystalizing. Whatever you decide to use -
Caramel Cheesecake Cupcake Filling
Beat 4 ounces cream cheese and ½ cup caramel sauce together until combined. (You'll see me use a spatula/whisk in the video; this step would've been *much* more easily done with a hand or stand mixer if I’d thought of that a little sooner!)
Cream Cheese Buttercream Frosting
Beat together softened cream cheese and butter; slowly add in powdered sugar alternating with milk until frosting reaches a pipeable consistency. Add vanilla and salt if needed and beat until well combined.
Assembly
Once the cupcakes have cooled, core them. (You can use a cupcake corer, the back end of a large piping tip, or....you can do what I do and cut the cores out with a plastic knife. Up to you!) Fill cupcakes with cheesecake filling, using a piping bag or a spoon.
Decorating
Transfer frosting to a large piping bag fitted with a star tip. Pipe frosting in large swirls onto your cupcakes.
Decorate the top of each frosting swirl with a caramel square, and add a drizzle of caramel sauce. Add sprinkles if desired! (I add sprinkles to everything at every opportunity, but that’s just me. ;) )
Done and done! Enjoy!
Video
Notes
(Please note nutrition information is an estimate and may not be exactly accurate.)