Preheat the oven to 350 degrees F. Place an oven shelf on the center rack. Line a standard cupcake pan with liners and spray very lightly with baking spray. I recommend spraying from above with your arm at a distance.
In a medium-sized bowl, whisk together the flour, baking powder, salt, and cocoa powder. In a small bowl or liquid measuring cup, combine the half-and-half and vanilla extract.
In a stand mixer fitted with the paddle attachment, cream the butter and sugar together on high speed for 3-5 minutes, until light and fluffy (to avoid splatters, start with a lower speed and work up to high). Scrape down the side of the bowl, then add the eggs on low speed, one at a time, scraping down the sides all the way to the bottom of the bowl after the 1st and 2nd egg, until they’re completely incorporated.
On medium-low speed, alternate between adding the dry and wet ingredients over the course of 30-60 seconds, starting and ending with the dry ingredients, until everything is just combined. Give the bowl one more scrape, all the way to the bottom, to make sure there are no patches of flour or butter. If the batter looks slightly broken, turn the mixer back on high speed for around 10-15 seconds, which will bring it back together.
Evenly distribute the batter between the cupcake liners. They should each be no more than halfway full. You may have a bit of excess batter.
Bake for 18-22 minutes, or until the center of one of the cupcakes comes out clean with a toothpick. Allow to cool completely before removing from the pan.
Prepare the Frosting
With an electric hand mixer or stand mixer fitted with the paddle attachment, whip the butter on medium speed until light and fluffy, 2-3 minutes.
Add the confectioners’ sugar, half-and-half, and vanilla. Mix on low speed for 1 minute, then increase the speed to medium-high and whip for 2-3 minutes, until smooth and creamy.
If the frosting is too thin, add additional sugar, 1/4 cup at a time. If it’s too thick, add more half-and-half, 2 tablespoons at a time.
Assemble the Cupcakes
Slice the stem end from each strawberry, creating a flat surface to sit on the cupcakes.
With a star piping tip (I used a Wilton 2D tip), frost each cupcake in a circular motion from the outside to the center. Don’t add height the way you would with a normal cupcake; aim for a single, flat layer.
Top each cupcake with a strawberry, flat-side down.
Pipe a small amount of frosting on the tip of each strawberry (I used a Wilton 10 tip).
Cupcakes are best served at room temperature. Store leftovers in an airtight container in the refrigerator and enjoy within a few days.
Whole milk or heavy cream can be substituted for the half-and-half in the vanilla buttercream.