Pumpkin Cupcakes with Rolos and Apple Cider Buttercream

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All the great Fall flavors packed into one cupcake! This pumpkin cupcake has a gingersnap cookie at the bottom, a Rolo candy in the middle (from trick or treating, obvs), and a pile of apple cider buttercream on top! Tastes like October.

These cupcakes also work really well as mini cupcakes. Makes about 20 regular-sized cupcakes, and nearly 40 mini cupcakes (depending on the size of your mini cupcake pan).

For the cupcakes you’ll need:

1 1/2 sticks unsalted butter, room temperature
1 1/2 c. granulated sugar
3 eggs
2 t. baking powder
1/2 t. baking soda
1/4 t. salt
2 t. vanilla
1 c. canned pumpkin
2 3/4 c. flour
1 c. whole milk
20-24 pieces of Rolo candies
20-24 gingersnap cookies

For the buttercream you’ll need:

2 sticks unsalted butter
2 c. powdered sugar
2 packets of instant apple cider mix
2 T. whole milk

Directions:

Pre-heat the oven to 350 degress (F).

Start with the cupcakes. Cream together the butter and sugar until well combined. Beat in the eggs, one at a time, and then the baking soda, baking powder, vanilla, and a salt. Stop the mixer and scrape down the sides, to ensure everything is getting mixed up really well. Beat for about 30 seconds, until the mixture is good and creamy, then add the pumpkin. With the mixer on low speed, add the flour and the milk, alternating between the two ingredients about a half cup at a time. Beat until the mixture is smooth and an even orange color.

Place a gingersnap cookie in the bottom of eat paper-lined cupcake tin (if they’re too big, you might have to trim off the edges with a sharp knife—if you do that, save the scraps to sprinkle on top!). Fill the cupcake tins about 3/4 of the way full, then press a Rolo candy into the center, covering with the batter. (Spoon an extra little drop of batter on top, if there isn’t enough to cover the Rolo completely.)

Bake for about 25-27 minutes until the cake is set. It should spring back up when you gently press your finger into the top of it (using a toothpick to test is no good—you have a molten Rollo in the center, remember?). 

Allow to cool, then make the buttercream!

First, whip up the butter for about 30 seconds, so it’s all fluffy. Then add the powdered sugar, a half cup at a time, until it’s well combined and fluffy. Whip in the powdered apple cider mix, one envelope at a time, tasting between to make sure you don’t add too much. Whip for a good 30-45 seconds to get everything well mixed and fluffy. If needed, drizzle in some milk to smooth out the frosting. You don’t want it to be too stiff.

When the cupcakes are cool, frost them with the apple cider buttercream, then sprinkle some gingersnap crumbs on top.