Preheat oven to 375℉. Line 2 large baking sheets with parchment paper, set aside.
In a small bowl, combine 1 ½ cups flour, ½ cup cocoa powder, ½ teaspoon baking powder, and ¼ teaspoon salt. Set aside.
In the bowl of a standing mixer, or in a large bowl with a handheld mixer, beat 1 cup softened butter, ¾ cup brown sugar and ½ cup sugar until fluffy (about 2 minutes). Add 2 teaspoons vanilla and beat to combine.
Add dry ingredients to the bowl and beat on low speed, then increase to medium-high and beat until the mixture forms large crumbs and easily sticks together when pinched.
Measure out 1 tablespoon portions of dough and roll each into a ball.
Press the center of each cookie down gently with a round, 1 teaspoon measuring spoon or the back of a wooden spoon.
Place cookie sheets in refrigerator for 30-60 minutes to chill. This will prevent the cookies from spreading.
Bake in 375℉ oven for 5 minutes. Check cookies and reindent the wells in the center of the cookies. Be sure to use a spoon - cookies are hot.
Continue cooking for 4-5 more minutes until edges are lightly browned and cookies are set. If the wells puffed up again, gently press them back down with the teaspoon when you remove them from the oven.
Let cool on the baking sheet for 5 minutes before transferring to a wire rack to cool completely.