Preheat the oven to 350 degrees. Line a baking sheet with parchment paper.
Combine the flour, baking powder, baking soda, salt, and cinnamon in a bowl.
Beat the softened butter and brown sugar, scraping down the sides, until creamy, using a hand mixer.
Add the eggs and vanilla and mix until creamy.
With the mixer on low, add in the flour.
Mix in 1¼ cups of chocolate chips on low.
With a rubber spatula, gather the cookie dough in one cohesive spot in the bowl. Using a cooking scoop, scoop 3 tablespoons of dulce de leche into 3 distinct and separate places in the cookie dough.
Mix again on low just a few times so the dulce de leche ribbons are throughout the batter. Stop after 3-5 rotations.
Use the same cookie scoop to drop rounded balls on the prepared baking sheet a few inches apart.
Bake for 10-12 minutes or until crisp on the edges and soft in the middle. Side Note: The cookies may be mishaped a little bit because of the oozing caramel pieces, but they will taste so good!
Remove from the oven and immediately top each cookie with the remaining chocolate chips. Cool on a wire cooling rack.
If desired, when serving, drizzle the top with a bit of dulce de leche and a sprinkle of flaky sea salt; otherwise, serve as is. Enjoy!