Preheat your oven to 350°F and line a baking sheet with parchment paper. In a medium bowl, whisk together the flour, baking soda, salt, and espresso powder (if using). The espresso powder won't make these taste like coffee—it deepens and intensifies the chocolate flavor beautifully. Set this mixture aside and have all other ingredients measured and ready before you start mixing.

In a large bowl, beat the softened butter with the packed brown sugar and sugar together for about 3 minutes on medium speed until the mixture is light, fluffy, and noticeably pale. This creaming process incorporates air into the dough, which helps create a tender cookie with the right texture. I always use room-temperature butter for this step—it beats more easily and incorporates air better than cold butter.

Add the instant vanilla pudding mix, eggs (at room temperature), and vanilla extract to the creamed mixture. Beat for 2-3 minutes until everything is well combined and the mixture is smooth. The pudding powder dissolves and creates a rich, creamy base that adds moisture and subtle vanilla-pudding flavor to the cookies without requiring additional liquid.

Add the dry ingredient mixture from Step 1 to the wet mixture from Step 3, folding gently with a spatula until just combined. Don't overmix—stop as soon as you don't see streaks of flour. Overmixing can develop too much gluten, making the cookies tough instead of tender and chewy.

Gently fold the chocolate chips into the dough using a spatula until evenly distributed. Drop rounded tablespoon-sized portions of dough onto the prepared baking sheet, spacing them about 2 inches apart to allow for spreading. I like to use a cookie scoop here—it makes uniform cookies that bake evenly.

Bake for 10-12 minutes, until the edges are set and lightly golden but the centers still look slightly underdone—they should look just barely baked. Remove from the oven and let the cookies cool on the baking sheet for 2 minutes (this allows them to firm up slightly), then transfer them to a wire cooling rack. They'll continue to set as they cool and will have the perfect chewy-tender texture.