Hi-Hat Oreo Cupcakes

Evenly fill the cupcake liners. Fill each liner about two-thirds full to ensure even baking and uniform sizes. Because the chocolate batter is thin, I like to use a pourable cup!

Use a pastry bag for frosting. Use a pastry bag fitted with a large round tip to pipe the frosting onto the cupcakes. This allows for more precise control and professional-looking swirls.

Prep the cupcakes for dipping. Because you are working with warm chocolate, the frosting must be chilled and firm to prevent it from melting.

Sour cream: Another key ingredient to a soft and moist cupcake! Full-fat Greek yogurt is a great substitute.

Coffee: The coffee brings out more of a rich chocolate flavor. I use instant Folgers dissolved in hot water, but you could also use regular drip coffee, espresso, or cold brew. If you prefer to leave it out, use equal parts hot water instead.

Black cocoa powder: Like my Oreo brownies and Oreo cinnamon rolls, black cocoa powder is key to an authentic Oreo flavor! If you don’t have any, substitute it with equal parts Dutch-processed cocoa powder.

Find the full list of ingredients, measurements, and instructions in the recipe card below!

Step 1: Combine the wet ingredients. In a large bowl, whisk together the sugar, sour cream, and oil until combined. Then mix in the eggs and vanilla. (Image 1 below)

Step 2: Mix in the dry ingredients and coffee. Whisk in the sifted dry ingredients until almost combined. Then, whisk in the hot coffee. (Image 2 below)

Step 3: Scoop the cupcake batter. Fill the cupcake liners 2/3 full with the chocolate cake batter. (Image 3 below) Because it’s a thin batter, I recommend using a bowl with a spout to pour it!

Step 4: Bake the cupcakes. You’ll know they’re done baking when the tops spring back gently when touched. Let the pan cool on a wire rack for a few minutes, then remove them from the pan and let them finish cooling on the rack. (Image 4 above)

Step 5: Make the cookies and cream frosting. Using a stand or hand mixer is best! Beat the frosting for at least 2-3 minutes. This will incorporate air into it, resulting in a light and fluffy texture and increased volume! If you find you don’t have enough frosting for the cupcakes, it’s likely it wasn’t beaten long enough. (Image 5 below)

Step 6: Frost the cupcakes. Using a large round tip, gently squeeze the piping bag, moving your hand in a clockwise motion, swirling the frosting on top of itself before releasing pressure. (Image 6 below)

Step 7: Dip the cupcakes. Hold the cupcake upside down and dip it straight down into the melted chocolate, then lift it out gently, allowing any excess chocolate to drip off. It’s best to use a deep, large-mouthed cup, like a Pyrex or coffee cup. (Image 7 above)

Step 8: Roll in Oreo crumbs. Wait 20-40 seconds until the chocolate looks like it’s half set, then roll the side of the cupcake in extra crushed Oreos. (Image 8 above)

Make ahead: The chocolate shell is best on the day of serving. Over time, it will start to soften and sweat from the moisture in the buttercream. The entire cupcake can be baked and assembled 2-3 days in advance, although I recommend waiting to dip them until the day of serving!

Storage: Store leftovers in an airtight container in the fridge for 3-4 days.

Freezing: Freeze the frosted cupcakes in an airtight container for up to one month. I recommend waiting to dip them in chocolate until serving!