Preheat your oven to 350°F (177°C) and line a cupcake pan with 12 cupcake liners.

In a small mixing bowl, combine chocolate chips with dark cocoa powder and pour in boiling water. Stir until smooth and glossy, then set aside to cool slightly.

In a large bowl, whisk together all-purpose flour, granulated sugar, baking soda, and salt until fully combined.

Pour the cooled chocolate mixture into the dry ingredients and mix until just combined. Add vegetable oil, eggs, and vanilla extract; mix until smooth.

Fill the cupcake liners about two-thirds full with batter and bake for about 20 minutes. Check for doneness with a toothpick.

For the frosting, beat unsalted butter until light and fluffy, then gradually add powdered sugar, heavy cream, vanilla extract, and salt. Fold in crushed Oreo cookies.

In a microwave-safe bowl, combine chocolate chips with heavy cream. Heat in 15-second intervals until silky smooth, then cool to drizzle-able consistency.

Once the cupcakes are completely cool, pipe frosting onto each cupcake, drizzle with ganache, and top with a halved Oreo cookie.