1. Preheat oven to 350 degree Fahrenheit. Line muffin tins with cupcake liners.
2. Place the flour, sugar, dark brown sugar, baking soda, baking powder, salt, and pumpkin spice into a large bowl. Gently stir to combine. Add in the oil and pumpkin, and stir until incorporated. Mix in the eggs, one at a time. Add in the espresso mixture, and stir just until the batter in smooth.
3. Fill cupcake liners 3/4 full, and bake for 18 minutes (or until a toothpick comes out clean). Remove from oven and place on wire racks to cool.
4. While the cupcakes bake, prepare the pumpkin spice caramel. Turn stove onto medium heat, and place a pot over element. Pour in ¼ of the sugar. Using a heat proof stirring utensil, stir until sugar begins to melt into a clear liquid. Gradually add in the remaining sugar, in a few installments. Continue to stir, until the sugar is fully liquified, and has become an amber.
5. Turn off the heat. Mix in butter slowly, then stir in cream, salt, and pumpkin spice. Place in fridge to cool for 20 minutes, then pour into desired container. I put mine in a squirt bottle (for drizzling over cakes), but a mason jar or Tupperware container would work great too! The caramel will keep for several weeks in the fridge.
6. Next, prepare the cream cheese frosting. Beat the butter and cream cheese on a medium speed for 30 seconds, until smooth. Slowly add in the powdered sugar, 1 cup at a time. Alternate with small splashes of cream. Once fully mixed, add in the vanilla and salt, and beat on medium low until the ingredients are fully incorporated, and the desired consistency is reached. If the frosting is too thick, add in cream (1 teaspoon at a time). If the frosting is too thin, add in more powdered sugar (quarter of a cup at a time).
7. The last component to prepare is the espresso whipped cream, to garnish the cupcakes. Beat all ingredients on medium speed in the bowl of an electric mixer fitted with the whisk attachment, until soft peaks form. This can be made several hours in advance, and stored in the fridge until needed.
Once the cupcakes are fully cooled, it’s time to decorate them:
1. Use a circle cutter or large frosting tip to remove the center from each cupcake.
2. Fill the center of each cupcake with pumpkin spice caramel
3. Place the cream cheese buttercream into a piping bag fitted with a Wilton 1M (open star) tip.
4. Frost a large swirl on top of each cupcake.
5. Drizzle pumpkin spice caramel over the frosting, in a spiral patter. Be sure the caramel is cooled, or else it will melt the frosting.
6. Using a baby spoon, add a tiny dollop of espresso buttercream to each cupcake.
7. Carefully insert half a rolled cookie into the frosting at a 45-degree angle.
8. Lightly dust the cupcakes with a bit more pumpkin spice.