Position racks in upper and lower thirds of oven; preheat to 375°F. Line two baking sheets with parchment. In a medium bowl, whisk together flour, espresso powder, baking soda, and salt until the espresso is evenly distributed and no streaks remain.

In a large bowl, beat butter, brown sugar, and granulated sugar on medium speed until light and fluffy, about 3 minutes. The mixture should look pale and almost creamy, not gritty. Scrape down bowl and beater.

Beat in eggs one at a time, mixing until fully incorporated before adding the next. Add vanilla and beat 30 seconds more. The batter should look smooth and glossy.

Add dry ingredients all at once. Mix on low speed just until no flour streaks remain, about 30 seconds. Do not overmix. The dough will be thick and slightly sticky.

Add chocolate chips and fold in with a wooden spoon or spatula, pressing them into the dough to distribute evenly. If dough feels too soft, chill 15 minutes for easier scooping.

Scoop 2-tablespoon mounds of dough onto prepared sheets, spacing 2 inches apart. Bake until edges are set and golden brown but centers still look slightly underdone, 10 to 12 minutes, rotating sheets halfway through. The espresso makes these darker than typical cookies, so trust the edges, not the color.

Cool on baking sheets 5 minutes (they will finish cooking from residual heat), then transfer to wire racks to cool completely. Cookies keep in an airtight container at room temperature for 4 days.