Prep the pan: Heat oven to 350°F (175°C). Grease a 12-cup muffin tin or line with paper liners.
Mix the wet ingredients: In a bowl, whisk peanut butter, brown sugar, granulated sugar, egg, milk, and vanilla until smooth and glossy.
Combine the dry: In a separate bowl, whisk oat flour, baking soda, baking powder, and salt to break up any lumps.
Bring it together: Add dry ingredients to wet. Stir with a spatula until just combined.
The dough will be thick, soft, and slightly sticky.
Portion: Scoop about 1 1/2 tablespoons of dough into each muffin cup. Lightly press to flatten the tops.
Create the wells: Use the back of a spoon or your thumb to press a shallow indent in the center of each portion.
Bake: Bake 9–11 minutes, until the edges are set and the centers look slightly underdone. Do not overbake—they’ll continue to set as they cool.
Fill and set: Immediately add your filling to the warm centers (press in a chocolate or spoon a little jam). Let the cookie cups cool in the pan 10–15 minutes before transferring to a rack.