Whisk the flour, cinnamon, baking soda, and salt together in a medium bowl and set aside.

In a large bowl using a handheld or stand mixer fitted with a paddle attachment, beat the softened butter and both sugars together on medium-high speed until creamy and smooth, about 2 minutes.

Add the eggs, molasses, and vanilla extract and beat on high speed until combined, about 1 minute, scraping down the sides as needed.

Turn the mixer to low speed and add the dry ingredients, mixing until just combined.

Add the oats and chocolate chips and mix on low speed or by hand until evenly incorporated.

Cover the dough and chill in the refrigerator for at least 45-60 minutes to prevent overspreading.

Preheat oven to 350°F (177°C) and line large baking sheets with parchment paper or silicone baking mats.

Scoop rounded tablespoons of dough (about 2 tablespoons per cookie) onto the baking sheets, spacing them 2 inches apart.

Bake for 10-12 minutes until the edges are lightly browned and the centers still look slightly soft.

Allow cookies to cool on the baking sheet for 5 minutes before transferring to a wire rack to cool completely.