1. Prepare Cookie Dough: Melt butter and whisk in molasses, dark brown sugar, and granulated sugar. Add eggs and vanilla extract, whisking until smooth. Stir in dry ingredients (flour, baking powder, baking soda, and spices) until dough forms. Alternatively, cream softened butter and sugars until light and fluffy, add egg and vanilla, then mix in dry ingredients carefully to avoid overmixing.

2. Shape and Chill Dough: Form approximately 70-gram balls of dough. Chill for 30 minutes in the fridge or 10 minutes in the freezer. Roll dough balls in granulated sugar, then press an indent into each ball using the back of a teaspoon (or thumb) while dough is still pliable. Chill again for 20-30 minutes in the freezer or 1-2 hours in the fridge. Dough can also be frozen after balling and indenting for longer storage.

3. Prepare Pumpkin Pie Filling: Whisk together pumpkin puree, heavy cream (or evaporated milk), half an egg, sugars, vanilla extract, salt, spices, and cornstarch until smooth. This mixture can be prepared up to 24 hours in advance and refrigerated.

4. Bake Cookies: Preheat oven to 365°F (or 350°F depending on recipe variation). Place 5-6 cookies on a lined baking sheet. Spoon 1-2 teaspoons of pumpkin filling into each indent without overfilling. Bake for 12-14 minutes until cookie edges are set and filling looks firm. Some recipes bake cookie cups first (about 10 minutes), then add filling, and bake an additional 9-15 minutes until golden and set.

5. Cool and Finish: Cool cookies on the baking sheet for about 10 minutes, then transfer to a wire rack to cool completely. Optionally, beat powdered sugar, vanilla, nutmeg, and cold heavy cream until stiff peaks form to top cookies with whipped cream just before serving.