Heat the oven & prep pans. Preheat to 350°F (175°C). Line a 12-cup muffin tin with paper liners.

Whisk dry ingredients. In a medium bowl, sift or whisk together flour, cocoa, baking powder, baking soda, and salt until uniform.

Combine wet ingredients. In a separate large bowl, whisk the granulated and brown sugars with the oil. Add eggs one at a time, then beat in the cooled coffee, milk, and vanilla until smooth.

Fold together. Pour the dry mix into the wet mixture in two additions and stir gently until just blended — avoid overmixing to keep the crumb tender.

Portion and bake. Divide batter between liners (about 2/3 full). Bake 18–20 minutes, or until a tester comes out with a few moist crumbs. Cool cupcakes on a rack.

Make the coffee cream. Chill a mixing bowl and beaters. Whip the cold cream with powdered sugar and instant coffee until stiff peaks form. Transfer to a piping bag fitted with a round tip.

Core and fill. Use a small corer or knife to remove a little cake plug from each cupcake. Pipe the coffee cream into the cavity until full. (Replace the plug if you like a covered top.)

Prepare the ganache. Heat the cream until it just simmers. Pour over the chopped chocolate and let sit 1 minute, then stir until glossy and smooth. Cool briefly until slightly thickened.

Finish the cupcakes. Spoon or drizzle ganache over each filled cupcake. Allow the ganache to set before serving.