In a medium sized saucepan add the sweetened condensed milk, pumpkin puree, butter and cinnamon. Cook over a medium heat and stir constantly. The mixture needs to come to a low boil and cook. Don’t stop mixing.
Cook until it starts to get thick, about 5-7 more minutes. You should be able to run a silicone spoon on the bottom of the pan and the mixture separates and forms back together after a few seconds.
Once it starts taking about 5-8 seconds to come together, turn off the heat and put the mixture on the plate or in a large bowl. Let it cool a bit and then place it in the fridge for 1 hour.
Pour the sugar into a bowl and set aside, line a tray with parchment paper and set aside and grab a toothpick.
Butter your hands up or use spray oil, grab about 2 tbsp worth of the mixture and roll into a ball, dip and roll in the sugar and place on the tray, repeat until you have no more mixture left.
Once all the balls are rolled and dipped into sugar take the toothpick and place your thumb slightly on the top of the ball, take the toothpick and slightly push the side of it into the ball to make the lines like a pumpkin, repeat all around the ball and to the other ones. It’s okay if your thumb slightly makes a dent in the top of the pumpkin, it needs it.
Once all the lines are added take a chocolate chip and place it on the top middle of the pumpkin and slightly push down just a tiny bit. Serve and enjoy!