Preheat oven to 350 degrees. Line your cupcake tins with cupcake papers.
In a medium mixing bowl, add in the melted butter and red wine.
Add in the vegetable oil and cocoa powder and whisk until smooth.
Add in the sour cream, vanilla extract, and eggs. Continue to whisk until incorporated.
In a separate bowl, add in cake flour, sugar, baking soda, and baking powder. Whisk until combined.
Pour the cocoa mixture in with the dry ingredients. Whisk until everything is combined. Try to whisk out most of the lumps.
Scoop the batter into the liners. I filled mine ¾ full.
Bake for 17 - 18 minutes or until they're done. Place a toothpick in the center of the cake and if it comes out clean or with moist crumbs it's done.
Let the cupcakes cool completely.
Frosting
Add ⅓ cup fresh raspberries into a blender. I used my bullet which does a pretty good job. Blend until smooth. Use a cheese cloth or fine mesh strainer and strain out the seeds. Set aside.
In a large mixing bowl, add in the butter and cocoa powder. Mix on medium until light and fluffy.
Add in the extract, 2 tablespoons pureed raspberries, milk and powdered sugar. Mix on low until nearly incorporated. Turn the mixing on high and let whip until light and fluffy about 2 minutes.
Add the frosting into a piping bag with a straight tip and pipe swirls on top of the cooled cupcakes.
Add a fresh raspberry to the top of each cupcake.
Notes
To store any leftover red wine chocolate cupcakes, place in an air tight container and store in the refrigerator for up to 3 days. You want to make sure the frosting is refrigerated as it contains milk.