In a large bowl cream together butter, brown sugar, and 2/3 cup sugar. Add vanilla, and pumpkin puree and mix until smooth.
In a medium bowl whisk together flour, pumpkin pie spice, salt, and baking powder.
Add dry ingredients to wet ingredients and mix until combined. Chill dough for 30 minutes.
Roll dough into 1 inch balls. Gently push 1 Rolo candy into one of the dough balls. Press a second ball on top of the Rolo candy and roll the whole thing into one ball. Repeat with remaining dough and Rolo candies.
Whisk together remaining 1/4 cup sugar and cinnamon. Roll dough balls in cinnamon sugar mixture. Place on a greased baking sheet and gently press to flatten slightly.
Bake at 375 for 8-10 minutes until very lightly browned. Allow to cool at least slightly before serving ( caramel centers will be hot). Store in airtight container.