In a medium, microwavable safe bowl, add the flour and warm in the microwave for 30 seconds. Once done, remove from the microwave and whisk because this will harden the flour slightly.
In a separate, medium sized bowl, combine the butter and brown sugar. Add in the pumpkin puree and mix until smooth.
Add the cinnamon, pumpkin pie spice, and vanilla extract and combine.
Pour in the flour and combine until a dough starts to form.
Fold in the chocolate chips and cover the bowl and place in the refrigerator for 8 hours or overnight.
Remove the cookie dough from the fridge and using a cookie dough scoop, scoop dough into 1-inch balls and place on a plate (lined with parchment paper) and freeze while you melt the chocolate.
Melt the chocolate with the oil in a microwave-safe bowl in 30 second increments until smooth.
Remove cookie dough balls from the freezer and dip each in chocolate and place back on the plate covered in parchment paper.
Freeze for 10 minutes or until the chocolate hardens. Remove from the freezer and enjoy!