Preheat your oven to 350°F (175°C) and position the rack in the center. Line a 12-cup muffin tin with cupcake liners.

In a large bowl, whisk together the flour, sugar, cocoa powder, baking soda, and salt, making sure to break up most of the cocoa lumps.

In a separate bowl, whisk together the coffee, vinegar, oil, egg, and vanilla extract until well combined.

Gradually add the wet ingredients to the dry ingredients, whisking gently until just blended. The batter will be slightly loose and may have small lumps—this is normal.

Divide the batter evenly among the prepared cupcake liners, filling each about two-thirds full. Avoid overfilling.

Bake for 20-22 minutes or until a toothpick inserted in the middle comes out clean.

Allow the cupcakes to cool in the pan for about 5 minutes before transferring them to a wire rack to cool completely. While cupcakes are cooling, prepare the frosting.

Using a food processor or blender, process raspberries into a fine powder.

Sift out seeds, using a fine mesh strainer (it’s okay if a few seeds get by)

In a large bowl, using a hand or stand mixer on medium/high speed, beat butter until creamy.

Add raspberry powder, vanilla and half and half to butter and continue to beat on medium speed until fully combined.

Slowly add the powdered sugar, continue beating on low speed until all of the sugar is combined, then turn up the mixer to high speed and continue beating another 1-2 minutes until smooth and fully combined.

Spread or pipe frosting on cooled cupcakes. Top with fresh raspberries, if desired.