Make the filling: Beat cream cheese, 1/4 cup sugar, and 1/2 tsp vanilla until smooth. Shape into a log, wrap in plastic, and freeze for 1-2 hours until firm.

Make the dough: Whisk flour, cocoa, baking soda, baking powder, and salt in a medium bowl.

In a large bowl, cream softened butter, 3/4 cup granulated sugar, and brown sugar until light and fluffy, about 2-3 minutes.

Beat in the egg, then the buttermilk, 1 tsp vanilla, and red food coloring until the batter is uniformly red.

Gradually add the dry ingredients to the wet, mixing on low until just combined. Cover and chill dough for 30 minutes.

Preheat oven to 350°F (175°C). Line baking sheets with parchment paper.

Remove firm filling from freezer and slice into 12 pieces. Flatten a scoop of dough, place a filling piece in the center, and wrap dough around it, sealing completely. Roll into a ball and place on baking sheet, 3 inches apart.

Bake for 11-13 minutes, until edges are set and centers are still soft. Cool on pan for 5 minutes, then transfer to a wire rack to cool completely.

For the glaze (optional): Whisk powdered sugar, 1 tsp milk, and vanilla. Add more milk as needed to drizzle. Drizzle over cooled cookies.