Preheat the oven to 350°F. Line a cupcake pan with liners.
To make the batter: In the bowl of a stand mixer fitted with the paddle attachment, add the butter, cane sugar, and vanilla extract. Mix on low until combined and there are no chunks of butter.
Add the eggs, milk, and sour cream and mix for a few rotations. It will look like cottage cheese at this stage. Make sure to scrape down the sides of the bowl to get the sugar that sticks to the bowl.
In a separate bowl, add the cake flour, baking powder, and sea salt and whisk together. Add the cake flour mixture into the mixing bowl and mix on low until combined. Scrape down the sides of the bowl and mix again to combine completely. Using a spoon or cupcake scoop, fill cupcake liners three-quarters full.
Bake for 20 to 25 minutes or until a toothpick inserted in center comes out clean. Allow to cool completely in the cupcake pans. (If you're baking at high altitude, be sure to check the Notes at the bottom of the recipe for high altitude baking instructions).
To make the frosting: In the bowl of a stand mixer fitted with the paddle attachment, add the shortening, powdered sugar, vanilla extract, and milk. Mix on low until combined, then speed mixer up to high and mix for 1 minute or until light and fluffy. Scrape down the sides of the bowl and mix again until light and fluffy. Start with less milk, then add more to get the consistency that you like and you can easily pipe out.
Transfer the frosting to a piping bag with Ateco tip #808. Add a small amount of frosting into a small bowl (this is for the frosting/snow on the North pole).
Add the white decorating sugar to a small bowl. Break off the curved parts of the candy canes.
Pipe a dollop of frosting onto a cupcake, then roll it in the white decorating sugar. This can be very freeform and I like how the mound can be in the middle or on the side, like a snowdrift. So, just let these be however they are!
Dip the top of one of the broken off candy canes in the bowl with the the additional frosting. Then dip the frosting part in the white decorating sugar. Stick the cupcake with the North pole anywhere that you like. I put mine kind of on the side of the cupcake.