Preheat oven to 375 degrees Fahrenheit and line a sheet pan with parchment paper.
In a large bowl using a hand mixer, whisk the butter, brown sugar, and 2/3 cup sugar until light and whipped. Add the vanilla, and pumpkin puree and mix until smooth.
In a medium bowl whisk together flour, pumpkin pie spice, salt, and baking powder.
Add the flour mixture to the butter mixture and mix until combined. Chill the dough for 30 minutes.
Roll the dough into 1-inch balls, and gently push 1 Rolo candy into each of the dough balls. Press a second ball on top of the Rolo candy and roll the whole thing into one ball. Repeat with the remaining dough and Rolo candies.
Whisk together the remaining 1/4 cup sugar and cinnamon. Roll the dough balls in the cinnamon sugar mixture.
Place the assembled dough balls on the prepared pan and gently press to flatten slightly.
Bake for 8-10 minutes until very lightly browned. let the cookies cool a few minutes before serving ( caramel centers will be hot).