Line two large baking sheets with parchment paper or use non-stick baking mats.
In a large mixing bowl, cream together butter and sugars until pale and creamy.
Add in your vanilla, milk and espresso powder; mix on high until combined.
Add in your egg and beat on high until fluffy, scraping the sides of the bowl as needed.
In a small bowl, whisk together flour, baking soda, salt and cinnamon.
Add dry ingredients to the wet ingredients and beat on low until it starts to come together; increase the speed and beat until completely combined.
Add in your dark chocolate chips and mix to combine.
Use a large cookie scoop to portion the dough into about 36 balls. Refrigerate the dough balls for at least 1 hour before baking.
Bake the cookies for 8-10 minutes.
Allow the cookies to cool for 3 minutes on the pan, then move to a wire rack to cool completely.
Store in an airtight container.
The calories shown are based on the recipe making 36 cookies, with 1 serving being 1 cookie. Since different brands of ingredients have different nutritional information, the calories shown are just an estimate. **We are not dietitians and recommend you seek a nutritionist for exact nutritional information.**