Preheat oven to 350F and prepare cupcake trays by lining with cupcake liners.
In small saucepan over medium heat, combine 1 cup milk and dark chocolate, stirring until chocolate is completely melted.
1 cup +3 Tablespoons whole milk, 3.5 oz quality dark chocolate
Increase heat to medium-high, stir constantly until mixture begins to bubble and stir in cocoa powder. Remove from heat and whisk until smooth. Set aside.
½ cup dark cocoa powder
In KitchenAid, combine canola oil and sugars, beat on medium speed for about 30 seconds, scrape sides of bowl, and stir again on medium-high speed for another 30 seconds -- until ingredients are well-combined (mixture will be very thick and grainy).
½ cup canola oil, ½ cup granulated sugar, ½ cup packed brown sugar
Add egg and vanilla, beat well.
1 large egg, 1 teaspoon pure vanilla extract
In a separate bowl, combine flour, baking powder, baking soda, and salt.
1 cup All-purpose flour, ¾ teaspoon baking powder, ½ teaspoon baking soda, ½ teaspoon salt
With mixer on low-medium speed, gradually stir in flour mixture to butter/sugar mixture, pausing to scrape down the sides of the bowl occasionally.
Pour the cocoa/dark chocolate liquid into the mixer and beat on medium speed until combined.
Scrape down sides of bowl and add 3 Tbsp milk, stir on medium speed again so all ingredients are combined.
Pour batter into cupcake liners, filling cupcake liners ⅔ of the way full.
Bake on 350F for 18 minutes (toothpick inserted into middle of cupcake should come out clean).
Allow to cool completely before frosting.
Raspberry Frosting
First, prepare a raspberry reduction by combining raspberries and sugar in a small saucepan over medium-low heat.
1 cup raspberries, 2 Tablespoons granulated sugar
Once berries begin to release their juices, increase heat to medium-high and stir constantly, mashing the berries with the back of your spoon as you go. Bring to a boil (still stirring constantly) and cook 6-8 minutes until mixture has reduced.
Run through a strainer to remove seeds and pulp (I add 1 Tbsp of seeds back in to the juices for a little bit of texture, this is optional) and allow to cool completely before using in frosting. Discard leftover seeds/pulp.
Once raspberry juices have cooled completely, prepare the frosting by creaming butter until smooth.
1 cup butter
Gradually add powdered sugar and stir until combined.
3 cups powdered sugar
Add in raspberry juices and stir well.
Spread or pipe frosting on top of cooled cupcakes.
Keep uneaten cupcakes stored in the refrigerator in an airtight container.