Pat the pumpkin dry. Place the pumpkin puree on a few layers of paper towel and gently press with more towels to remove excess moisture. This keeps the cookies from turning cakey. You should still have about 1/3 cup after blotting.

Prep the caramels. If using heavy cream, toss caramels with cream and let them sit for 5 minutes. This softens them so they melt smoothly. Pat off any excess and set aside.

Mix the wet ingredients. In a large bowl, whisk melted butter, brown sugar, and granulated sugar until glossy. Whisk in the blotted pumpkin, egg yolk, and vanilla until smooth.

Combine dry ingredients. In a separate bowl, whisk flour, baking soda, baking powder, salt, cinnamon, ginger, nutmeg, and cloves.

Make the dough. Add dry ingredients to wet and fold with a spatula just until no dry streaks remain. The dough will be soft but not runny.

Chill. Cover and refrigerate for 45–60 minutes. Chilling firms the dough and keeps the cookies thick.

Preheat and prep. Heat oven to 350°F (175°C). Line two baking sheets with parchment paper or silicone mats. Stir together the cinnamon-sugar for rolling in a small bowl.

Form the cookies. Scoop about 2 tablespoons of dough (a heaping medium scoop). Flatten slightly in your palm, place a caramel in the center, and wrap dough around it, pinching seams to seal completely. Roll into a smooth ball, then roll in cinnamon-sugar. Repeat with remaining dough and caramels.

Bake. Arrange 2 inches apart on the baking sheets. Bake 10–12 minutes, or until the edges look set and the tops are slightly puffed and matte. The centers should look soft but not wet.

Shape and cool. If cookies spread unevenly, use a round glass or cookie ring to shimmy them into neat circles while hot. Cool on the sheet for 10 minutes, then transfer to a rack. The caramel will be very hot—let it settle before biting.