Preheat Oven and Prepare Baking Sheets: Preheat your oven to 350°F. Line two baking sheets with parchment paper or lightly grease them.
Cream Butter and Sugars: In a large bowl, cream together the softened butter, light brown sugar, and sugar until the mixture is light and fluffy.
Add Pudding Mix and Wet Ingredients: Beat in the instant vanilla pudding mix until well blended. Add the eggs and vanilla extract, and continue to mix until well incorporated.
Combine Dry Ingredients: In a separate bowl, whisk together the flour, cinnamon, baking soda, and salt.
Mix Dry Ingredients into Wet Mixture: Gradually add the dry ingredients to the wet mixture and stir until just combined.
Fold in Oats and Chocolate: Gently fold in the old fashioned oats and 1 cup of the semisweet chocolate chips. (feel free to measure the chocolate chips with your heart!)
Form Cookies: Drop ½ inch rounded spoonfuls of the dough onto the prepared baking sheets. (I use a cookie scoop for this and it's super easy). Press a few of the remaining chocolate chips on top of each cookie for extra chocolatey goodness.
Bake: Bake in the preheated oven for 10-12 minutes or until the edges turn a light golden brown. (The key to keeping them chewy is not to over bake)
Cool: After taking them out of the oven, lightly press 4-5 chocolate chips into the top of each cookie. Allow the cookies to cool on the baking sheet for about 5 minutes, then transfer them to a wire rack to cool completely.