Preheat & Prep: Preheat oven to 350°F (175°C). Line a baking sheet with parchment paper.
Mix Dry Ingredients: In a medium bowl, whisk together flour, crushed raspberries, baking powder, and salt.
Cream Butter & Sugar: Beat softened butter and granulated sugar in a large bowl with an electric mixer until fluffy, about 2 minutes.
Add Wet Ingredients: Beat in the egg and vanilla extract until fully combined.
Combine Mixtures: Gradually mix the dry ingredients into the wet mixture. Gently fold in chocolate chips using a spatula.
Create Espresso Swirl: Drizzle the espresso mixture over the dough. Swirl it with a spatula, but don't overmix — messy is good.
Shape Cookies: Drop tablespoon-sized scoops of dough onto the baking sheet, leaving about 2 inches of space between each.
Bake: Bake for 9-10 minutes or until the edges are just set.
Cool: Allow cookies to cool on the baking sheet for 5 minutes. Transfer to a wire rack to cool completely.