Pumpkin Pie Cookie Cups
Molasses cookie cups are filled with delicious pumpkin pudding then topped with fresh whipped cream, everyone will love this delectable fall recipe!
Equipment
- Stand Mixer
- Mini cupcake pan
- Cookie sheet
- Medium Cookie Scoop
- Hand mixer
Ingredients
Spiced Molasses Cookie Cups
- 3/4 cup unsalted butter softened or vegan butter sub
- 1/2 cup brown sugar
- 1/2 cup granulated sugar
- 1/3 cup molasses
- 1/4 cup 2/% milk or vegan milk sub
- 1 tsp vanilla extract
- 2 1/4 cups all-purpose flour or bobs red mill gluten-free baking flour
- 2 tsp baking soda
- 1 1/2 tsp ground cinnamon
- 1 tsp ground ginger
- 1/2 tsp ground cloves
- 1/4 tsp ground all spice
- 1/2 tsp salt
Filling
- 3/4 cup prepared pumpkin pudding homemade or jello brand
- 1 cup heavy whipping cream or silk heavy cream alternative for vegan sub
- 1/8 cup confectionary sugar
- 1/2 tsp vanilla extract
Instructions
- For the cookie cups, in a small to medium bowl whisk flour, baking soda, salt, and spices, set aside.
- Preheat oven to 350°. Spray two mini cupcake pans with pam baking spray (48 total indentations) then line 1 cookie sheet with parchment paper and set aside.
- In the bowl of a stand mixer, cream butter, brown sugar, and granulated sugar until light and fluffy. Then beat in the molasses, milk, and vanilla extract.
- Gradually beat flour mixture into creamed mixture.
- Using a medium cookie scoop create rounded dough balls, add one ball to each of the 48 mini cupcake indents and slightly press the balls down into the indent, don’t make a well just a lightly push down. With the remaining dough, you should get 12 more dough balls, place them 2-in. apart on parchment-lined baking sheets. Slightly smoosh down with your hand.
- Bake twelve cookies, take 10-15 minutes, or until edges begin to set. The cookie cups take 20-25 mins to bake. Cool the twelve cookies on pans for 5 minutes. Remove to wire racks to cool completely. When cookie cups are set take them out and while still hot create an indent with the handle of a wooden spoon. Cool the cookie cups in the pan for 5 mins-10 mins, until you can take them out of the cups, allow to cool completely on the counter or wire racks.
- If you haven’t already made your Pumpkin pudding do so, you can use my homemade pumpkin pudding recipe or Jello brand, make sure your pudding is set prior to assembly.
- If making whipped cream, with your hand mixer or whisk whip heavy cream, sugar, and vanilla extract until whip cream texture.
- For a neat assembly, you will want to grab 2 small/medium Ziplocs or 2 pipping bags. Line 2 short cups with the opened Ziplocs and fill one with pudding and one with whipped cream. Close the bags making sure to release the air inside.
- Take the pumpkin pudding bag and cut a piece small off of one of the bottom corners, then pipe into cookie cups.
- Once you are done evenly filling the molasses cookie cups with pudding, cut a smaller piece off of one of the bottom corners of the whipped cream bag. Add a little squirt/dollop to the tops of each cookie cup and if you like having a little crumble on top crumble 1-2 cookies and sprinkle on top of each cup.
Notes
The recipe can make up to 60 cookie cups but I make 48 cups and 12 cookies so there are extra cookies on the side (two for the tops as garnish).
Make sure your pumpkin pudding is made on the same day you plan to serve the pumpkin pie cookie cups so the pudding is super fresh, pudding lasts 4 days.
The molasses cookie cups can be made a day or two in advance but do not fill them until the day you plan on serving (as the pudding sits in the cookie cup it will soften the cup, the longer they sit the softer they get).