In a medium saucepan, combine the sweetened condensed milk, pumpkin puree, butter, and cinnamon. Cook over medium heat, stirring constantly, until the mixture reaches a low boil and thickens. Continue stirring until the mixture pulls away from the sides of the pan and takes about 5-8 seconds to come together. Turn off the heat and transfer to a plate or bowl. Cool slightly, then refrigerate for 1 hour.
Pour sugar into a bowl and set aside. Line a tray with parchment paper. Butter your hands or use spray oil, then scoop about 2 tablespoons of the mixture and roll into balls. You can also use a scoop, which ensures even sizes. Roll each ball in sugar and place on the tray. Repeat until all the mixture is used.
Using a toothpick, gently press lines into each ball to create a pumpkin shape. If your thumb makes a small dent on top, it’s fine.
Place a chocolate chip in the center of each pumpkin and press down slightly. Serve and enjoy!
Notes
To check if the mixture is ready, run a silicone spoon along the bottom of the pan. It should take 5-8 seconds for the mixture to come back together.
Allow the mixture to cool slightly at room temperature before refrigerating. This helps it set more evenly.
Keep the truffles in an airtight container in the refrigerator. They can last up to a week and taste even better after a day or two.