Preheat your oven to 330°F and line two baking sheets with parchment paper. Measure out all your ingredients into separate bowls: the flour, baking powder, salt, chocolate chips, and espresso powder. Whisk the flour, baking powder, salt, and espresso powder together in a small bowl—this ensures the leavening and espresso distribute evenly throughout the dough without lumps.

In a large mixing bowl, combine the softened butter and sugar. Beat together for 2-3 minutes until the mixture becomes pale and fluffy—this incorporates air into the dough, which helps these cookies have a tender crumb. Add the vanilla extract and mix until fully combined.

Pour the condensed milk into the butter mixture and stir until completely incorporated. The condensed milk adds richness and helps keep these cookies moist and tender—that's what gives them their grandma-style softness. Gently fold in the dry ingredient mixture from Step 1, stirring just until the flour is no longer visible. Finally, fold in the chocolate chips until evenly distributed throughout the dough.

Using a kitchen scale or a cookie scoop, portion the dough into 20-gram balls and place them about 2 inches apart on the prepared baking sheets. Bake for 14-15 minutes until the edges are golden brown but the centers still look slightly underbaked—they'll continue to set as they cool. I find that removing them just before they look completely done keeps the insides wonderfully soft and chewy.

Let the cookies cool on the baking sheet for 10-15 minutes—this is crucial because they're still setting during this time and will firm up without becoming too crispy. Transfer them to a wire rack to cool completely, or enjoy them while still warm with a glass of milk.