To the bowl of a stand mixer fitted with the paddle attachment (or mixing bowl and hand mixer), add the butter and beat to soften and fluff it, about 1 minute.

Add ¼ cup granulated sugar, vanilla, and beat to cream ingredients until fluffy, about 3 to 4 minutes, stopping to scrape down the sides of the bowl as necessary.

Add the flour and mix to incorporate it. The dough will be very sandy, pebbly, and dry. Add two tablespoons of half-and-half or cream and mix. The dough will come together and it will be on the soft and sticky side. If your dough is sandy and dry and hasn’t come together, add 1 additional tablespoon of cream, or as needed, so it combines.

Wrap dough in plastic wrap and transfer it to an airtight container and refrigerate it for at least two hours, or up to five days, before rolling it out.

Turn the dough out onto a floured Silpat Non-Stick Baking Mat or floured countertop and cover it with a piece of plastic wrap to prevent it from sticking to the rolling pin. Roll dough out to about one-eighth inch thick.

Using a 2-inch cookie cutter or biscuit cutter, cut out the dough into rounds. Re-roll your scraps and use every last bit of dough until it’s gone.

Place rounds on a Silpat-lined, parchment-lined, or cooking sprayed baking sheet. If dough has gotten soft while rolling and cutting it out, cover and refrigerate the tray for about an hour.

Preheat oven to 350F. Before baking, place about ½ cup granulated sugar in a shallow bowl and dredge each dough round through the sugar and return sugared rounds to baking sheet. Piece each round three or four times with the tines of a fork.

Bake for 7 to 9 minutes or just until they've set, rotating trays halfway through baking.

Allow cookies to cool for about 5 minutes on baking trays before transferring to a wire rack to finish cooling.

While the cookies cool, make the buttercream. Beat one stick of butter to soften and fluff it, about 1 minute.

Add 1 ½ cups confectioners’ sugar, vanilla, and beat until soft and fluffy, about 5 minutes.

Add food coloring very slowly, in the color of your choice, and mix to incorporate.

Frost one cookie generously with 1 to 2 tablespoons frosting, top with another cookie, sandwich them together, and lightly squeeze.