Preheat oven to 350°F. Prepare cupcake pan with 12 liners and set aside.
In a large bowl, whisk together flour, cocoa powder, brown sugar, granulated sugar, baking soda, salt and cinnamon. Set aside.
1 cup all purpose flour | ½ cup cocoa powder | ½ cup light brown sugar | ½ cup granulated sugar | 1 teaspoon baking soda | ¼ teaspoon salt | Pinch of cinnamon
In the bowl of a stand mixer fitted with the paddle attachment, combine egg, buttermilk, olive oil and vanilla extract and mix on medium speed for about 15 seconds until somewhat combined.
1 egg | 1 cup buttermilk | ½ cup olive oil | ½ teaspoon vanilla extract
Add dry mixture to the bowl and combine on low speed, gradually increasing speed to medium, until completely combined. Add wine and beat to combine again.
½ cup red wine
Pour batter into prepared cupcake liners, filling ¾ full. Bake for 12-18 minutes, or until a toothpick inserted into the center of a cupcake comes out with a moist crumb.
Let cool in pan for 5 minutes, then transfer to wire rack to cool completely.
In a small saucepan over medium heat, combine blackberries, sugar and lemon juice, frequently stirring and squishing blackberries with the back of a spoon. Heat until blackberries are soft, about 5-7 minutes.
1 cup fresh blackberries | 1 teaspoon granulated sugar | Juice of 1 lemon
Push the mixture through a fine mesh strainer over a small bowl to remove all the seeds and chunks. Let the liquid cool completely - you can place it in the fridge to speed up the process.
In the bowl of a stand mixer fitted with the paddle attachment, beat butter until smooth. Add blackberry juice, salt and 1 cup powdered sugar and combine on low speed, gradually increasing speed to high, until completely combined and fluffy. Add more powdered sugar, ½ cup at a time, to taste. If you want to make your frosting's color more bold, add food coloring and beat to combine, one drop at a time, until you've reached your desired shade.
1 cup unsalted butter | ¼ teaspoon salt | 1 ½-2 cups powdered sugar | Gel food coloring
Spoon frosting into a piping bag fitted with the tip of your choosing and frost cooled cupcakes. Serve and enjoy!
Note #1: I like my frosting on the less sweet side, so I find myself only using around 1 ½ cups of powdered sugar in the frosting.Note #2: These are best served same day, but can be kept in the fridge for up to 3 days in an airtight container. Let come to room temperature before serving.