Step 1

In a saucepan, melt the butter over medium heat.

Step 2

Once melted, mix in the brown sugar and heavy cream. Bring the mixture to a simmer and let it bubble for 6 minutes.

Step 3

Remove from heat and mix in the salt, vanilla, and rum extract. It should look thin, dark, and slightly translucent.

Step 4

Pour into a glass and allow it to cool at room temperature while we make the cupcakes.

Step 5

Preheat the oven to 350F and line a cupcake tin with 12 paper liners.

Step 6

In a measuring glass, combine the milk and vinegar and set aside.

Step 7

In a medium-sized bowl, whisk together the flour, baking powder, baking soda, cinnamon, and salt. Set aside.

Step 8

In a large mixing bowl, whisk together the oil, sugar, and extracts. It should be clumpy like wet sand.

Step 9

Mix in 1/2 of the milk mixture, followed by half of the dry ingredients. Once smooth, mix in the rest of the milk, again followed by the rest of the dry ingredients. The batter should be fairly thin, but not watery.

Step 10

Pour the batter into each cupcake liner, filling about 3/4 full. Bake for 15-18 minutes or until a toothpick in the center comes out clean with a few moist crumbs.

Step 11

Allow the cupcakes to cool inside the pan for about 10 minutes, then transfer to a cooling rack to cool completely.

Step 12

In a large bowl using a hand or stand mixer with the whisk attachment, combine the butter with 1 cup of powdered sugar.

Step 13

Once smooth, continue to mix in the powdered sugar one cup at a time. When the mixture becomes too thick, mix in one tablespoon of milk.

Step 14

After all of the sugar is mixed in, add the vanilla and salt.

Step 15

Now have 4 separate bowls ready, filling each with 3 tablespoons of buttercream. Color each bowl with the individual house colors – red for Gryffindor, green for Slytherin, purple for Ravenclaw, and yellow for Hufflepuff.

Step 16

To the rest of the buttercream, mix in two tablespoons of the cooled butterscotch sauce and set aside.

Step 17

Split the cookies in half and remove the cream filling. Arrange the cookies, frosting side up, on a plate.

Step 18

Pipe the individual buttercream colors onto the cookies (each house gets 3 cookies), making a tall witch hat shape. Do so using a round piping tip, or a ziplock bag with a corner snipped off.

Step 19

Place the hats into the freezer to chill firm, about 30 minutes.

Step 20

When it gets close to the 30 minute mark, melt the chocolate and oil in a heat-safe container (preferably a 2 cup measuring glass) in the microwave. Heat in 30 second intervals, stirring between each time, until smooth. Allow it to cool for about 5-10 minutes.

Step 21

When the hats are firm, coat each one in chocolate. My preferred method is to stick a toothpick into the button of the hat. Then, tilt the container of chocolate so that it pools to one side. Dunk the hat into the chocolate and twirl to coat it all around. Lift it out and tap off any excess. Then, stick the toothpick into the bottom of a cardboard box so that the hat can dry without disrupting the bottom (see picture in post for reference).

Step 22

Otherwise, dunk the hats using a fork and place onto a plate to dry. Chill the hats for about 15 minutes to allow the chocolate to set.

Step 23

Pipe the butterscotch buttercream onto each cooled cupcake. Top with a drizzle of butterscotch sauce, followed by a sorting hat.

Step 24

Now take a bite to join your Hogwarts house!