Ingredients

Scale

3/4 cup (170 grams) salted butter (or unsalted as preferred)
1/3 cup molasses (regular, not blackstrap)
3/4 cup (163 grams) dark brown sugar, packed
3/4 cup (156 grams) granulated sugar
2 large eggs, at room temperature
1 1/2 teaspoons vanilla extract
3 1/4 cups (422 grams) all-purpose flour, spooned and leveled
1 teaspoon baking powder
1 teaspoon baking soda
1 teaspoon ground cinnamon
3/4 teaspoon ground ginger
1/4 teaspoon ground cloves
1/8 teaspoon ground nutmeg
1/4 cup granulated sugar (for rolling the dough)
Approximately 2 tablespoons beaten egg (about half a large egg)
1/4 cup plus 1 tablespoon (73 grams) canned pumpkin puree (fresh can also be used)
2 tablespoons heavy cream or evaporated milk
1/4 teaspoon vanilla extract
2 tablespoons dark brown sugar
Pinch of salt
1/2 teaspoon cinnamon
1/4 teaspoon ground ginger
Pinches of ground cloves, nutmeg, and allspice
1 teaspoon cornstarch or all-purpose flour (for thickening)
1/4 cup cold heavy cream
2 tablespoons powdered sugar
2 teaspoons vanilla extract
Pinch of nutmeg (optional)

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Instructions

1. Melt the butter in a large mixing bowl, then whisk in molasses, dark brown sugar, and granulated sugar until combined.
2. Add the eggs and vanilla extract; whisk until smooth.
3. In another bowl, mix dry ingredients: flour, baking powder, baking soda, cinnamon, ginger, cloves, and nutmeg.
4. Gradually stir the dry ingredients into the wet mixture until a dough forms.
5. Portion dough into 70-gram balls, roll in granulated sugar, and make an indentation in the center of each.
6. Chill the dough balls in the fridge for 30 minutes to 2 hours.
7. Preheat your oven to 365°F (185°C). Whisk together all ingredients for the pumpkin pie filling until smooth.
8. Spoon pumpkin filling into the cookie indentations.
9. Bake the cookies for 12–14 minutes until edges are set and filling is firm.
10. In a cold bowl, whip the cream with powdered sugar and vanilla until stiff peaks form.
11. Once cookies have cooled, pipe or dollop whipped cream onto each cookie.

Last Step:

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Notes

🕒 Chilling improves the texture and shape but is not mandatory for a quicker preparation.
🥥 Try using graham cracker crumbs in the dough for added flavor.
❄️ Dough can be refrigerated for up to 4 days or frozen for up to 2 months for future use.

Author: Brandi Oshea
Prep Time: 20 minutes
Chill Time: 30 minutes to 2 hours
Cook Time: 12-14 minutes
Category: Dessert
Method: Baking
Cuisine: American
Diet: Vegetarian

Nutrition

Serving Size: 1 cookie
Calories: 284
Sugar: 24g
Sodium: 160mg
Fat: 10g
Saturated Fat: 6g
Unsaturated Fat: 4g
Trans Fat: 0g
Carbohydrates: 45g
Fiber: 1g
Protein: 3g
Cholesterol: 35mg