Line a baking sheet with parchment paper or wax paper. Set aside.
In a medium size saucepan over medium heat mix the pumpkin puree, butter, maple syrup, milk, brown sugar, pumpkin spice, salt, and vanilla extract.
Heat and stir constantly until all the ingredients are melted and you have a smooth mixture. About 2 minutes cooking time.
Bring the sugar mixture to a full rolling boil and boil for 1 minute stirring occasionally so it does not stick to the bottom. ***(see notes below)
Take the saucepan off the heat and add the oats all at once.
With a large wooden spoon or heatproof rubber spatula mix all the easy cookie ingredients together until the oats are covered with the pumpkin mixture.
Take a medium cookie scoop and scoop the cookie dough into balls. Place them on the prepared cookie sheet. ***(see notes below)
You may keep them in the round ball shape or your may gently press on them so they look like a thick round classic cookie recipe.
Let the chewy cookies come to room temperature.
Store in an airtight container and keep in the fridge for up to 5 days.