Preheat oven to 350°F, line baking sheets with parchment paper or silicone baking sheets
Whisk flour, baking soda, cinnamon, pumpkin pie spice, salt, and oats together in a large bowl, set aside.
Combine melted butter, maple syrup, dark brown sugar, granulated sugar, egg yolk, blotted pumpkin puree, vanilla, and rum extracts together in a separate bowl. Stir until incorporated.
Pour wet ingredients into dry ingredients and mix to combine. Fold in the chocolate chips.
Scoop cookie dough onto baking sheets using a 1-2 tablespoon cookie scoop or spoon spacing cookies apart by 3 inches. Flatten each dollop slightly to allow for even spreading. Bake for 12-14 minutes or until lightly browned on the edges, the centers will still appear very soft.
Remove from oven and allow to cool on baking sheets for 5 minutes before transferring to a cooling rack. Enjoy!