RED VELVET COOKIE LAYER
1 and 1/2 cups + 1 Tablespoon (198g) all-purpose flour
1/4 cup (32g) unsweetened cocoa powder
1 teaspoon baking soda
1/4 teaspoon salt
1/2 cup (115g) unsalted butter, softened to room temperature.
3/4 cup (150g) light brown sugar (or dark brown)
1/4 cup (50g) granulated sugar
1 egg, at room temperature*
1 Tablespoon (15ml) milk
2 teaspoons vanilla extract
1 Tablespoon red food coloring (liquid or gel)
12 ounces (336g) full-fat cream cheese, softened to room temperature
2 Tablespoons (30g) yogurt*
1/3 cup (67g) granulated sugar
1 large egg, at room temperature
1 teaspoon vanilla extract
1/2 cup (90g) mini or regular semi-sweet chocolate chips
Preheat oven to 350F degrees. Line two 12-count muffin pans with cupcake liners. Set aside.
Make the red velvet cookie layer: toss the flour, cocoa powder, baking soda, and salt together in a large bowl. Set aside.
Using a handheld or stand mixer with a paddle attachment, beat the butter on high speed until creamy, about 1 minute.
Scrape down the sides and the bottom of the bowl as needed. Switch the mixer to medium speed and beat in the brown sugar and granulated sugar until combined.
Beat in the egg, milk, and vanilla extract, scraping down the sides and bottom of the bowl as needed. Once mixed, add the food coloring and beat until combined.
Turn the mixer off and pour the dry ingredients into the wet ingredients. Turn the mixer on low and slowly beat until a very soft dough is formed. Beat in more food coloring if you'd like the dough to be redder. The dough will be sticky.
Press 1 scant Tablespoon of cookie dough into the bottom of each cupcake liner. I say "scant" because otherwise you won't have enough to make 22-24 mini cheesecakes. Bake each batch for 8 minutes to pre-bake the crust before layering the cheesecake on top.
Make the cheesecake layer: using a handheld or stand mixer with a paddle attachment, beat the cream cheese on medium-high until completely smooth. Add the yogurt and sugar, beating on high until combined. Add the egg and vanilla and beat on medium until combined.
Try not to overbeat, which will cause cheesecake cracks. Gently fold in the chocolate chips. Dollop 1 Tablespoon of cheesecake batter on top of the pre-baked cookie, spreading it to make sure it completely covers the cookie.
Return the mini cheesecakes to the oven and continue to bake for about 20 more minutes, making sure the tops of the cheesecake does not get too brown. The cups are done in the oven when the cheesecake topping no longer jiggles when you shake the pan.
Cover the cups with aluminum foil if the tops are getting too brown too soon. Allow to cool for 30 minutes on the counter, then in the refrigerator to set for another 1.5 hours.
Cookie cups stay fresh covered at room temperature for 12-24 hours, and then must be refrigerated after that for up to 3 more days.