Preheat the oven to 375° and spray a cookie sheet with cooking spray.
Unroll one can of the crescent roll dough.
Combine the pumpkin puree, brown sugar, and pumpkin spice. Spread over the dough.
Unroll the remaining crescent roll dough over the pumpkin mixture.
Using a knife or pizza cutter, cut the dough in half, then each half in half again. Then divide each piece in half.
Cut each strip down the middle till ½ inch from the end. Twist each side over each other all the way down.
Take one end of the dough and make a circle about a third of the way. Place the end under the dough and twist it down the middle of the roll. Roll the remainder of the twist around the center and tuck the end under the roll.
Place the roll on the pan. Repeat with the remaining dough.
Brush the melted butter over the rolls. Combine the cinnamon and sugar together and sprinkle over the rolls.
Place in the oven and bake for 10 minutes, or until the rolls are lightly browned.
Place the powdered sugar, milk and vanilla in a bowl and use a whisk beat well.
Drizzle the icing over the rolls and serve.