Preheat oven to 350 degrees and line muffin tins with baking cups.
In a bowl of a stand mixer fitted with the paddle attachment or in a large bowl, mix together cake mix, instant pudding, sour cream, vegetable oil, eggs, milk, and vanilla. Mix very well. Gently stir in the chocolate chips with a spatula.
Equally divide the batter into the baking cups, filling 2/3 of the way full. Bake for 18-22 minutes, let cool for 5 minutes in pan, then remove and place them on wire cooling racks to cool completely.
In the meantime, make your buttercream by first melting the caramel candies and heavy cream in a small saucepan over medium heat. Once the caramel is all melted, stir in 1/2 tsp. of salt.
In the bowl of a stand mixer fitted with the paddle attachment, cream the butter until light and fluffy. Add in the remaining 1 tsp. of salt.
Gently add half of the powdered sugar to the butter and beat until light and fluffy. Then drizzle in the caramel while the mixer is on low. If the caramel has hardened up a bit that you can't pour it, heat it up just enough so you can pour it into the mixer with ease.
Add the remaining 2 cups of powdered sugar and beat until well combined.
Put the frosting in a piping bag fitted with a pastry tip of your choice.
Pipe the frosting on top of the cooled cupcakes.
Store cupcakes in an airtight container for up to 4 days.
The frosting won't be enough for you to pipe as much as I did on all the cupcakes. You might want to double the frosting if you want to pipe a lot like I did, or you can just pipe a tiny swirl :)
Salted Caramel Chocolate Cupcakes
Amount Per Serving (1 Cupcake)
Calories 383Calories from Fat 225
% Daily Value*
* Percent Daily Values are based on a 2000 calorie diet.