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Whisk the pumpkin puree, sugar, egg, cream, and spices in a medium bowl until smooth. Set aside; this will thicken slightly as it rests.
Using a hand mixer or stand mixer, cream the butter and brown sugar until pale and fluffy. Add egg yolks and vanilla, mixing until incorporated.
In another bowl, whisk together the gluten-free flour, xanthan gum, baking powder, salt, and spices. Gradually add this to the wet mixture and mix until the dough is smooth and scoopable, soft but not sticky.
Combine cinnamon and sugar in a small bowl. Scoop the dough with a 2-tablespoon cookie scoop, roll into balls, and coat in the cinnamon sugar mixture. Arrange them on a parchment-lined baking sheet, spaced 2 inches apart.
Using a 1-tablespoon measuring spoon, press an indent in the center of each cookie.
Spoon about 1 tablespoon of pumpkin pie filling into each indentation. The filling should reach the top without overflowing.
Bake in a preheated oven at 350°F (180°C) for 10–12 minutes, or until the edges turn golden and the filling is just set. Let the cookies cool completely on the baking sheet to firm up before removing.
Once cooled, pipe small dollops or swirls of whipped cream on top just before serving. A light sprinkle of cinnamon adds the final festive touch.