Dianne’s Pumpkin Cookie Cups: Cozy Fall Dessert Recipe

There’s something truly magical about the crisp air of autumn, isn’t there? The leaves turn vibrant hues, sweaters come out of storage, and suddenly, my kitchen smells like a spice factory in the best possible way. This time of year always brings back memories of sharing warm, homemade treats with loved ones. And let me tell you, Dianne’s Pumpkin Cookie Cups are about to become a cherished part of your fall traditions. If you’re looking for more delightful fall treats, you might also adore these soft pumpkin cookies.

These little gems are unbelievably easy to whip up, quick enough for a weeknight craving, and so memorable, your friends and family will be asking for the recipe every single year. Imagine a soft, slightly spiced cookie holding a creamy, dreamy pumpkin filling – pure fall bliss in every bite!

Why You’ll Love Dianne’s Pumpkin Cookie Cups

• Fast: Quick prep and bake time mean you’ll be enjoying these treats in no time.
• Easy: Simple ingredients and straightforward steps make this a perfect recipe for any baker.
• Giftable: Pack them up in a cute box, and you’ve got the most thoughtful homemade gift!
• Crowd-pleasing: Who can resist a tender pumpkin cookie overflowing with creamy, spiced pumpkin goodness?

Ingredients

• 2 cups all-purpose flour: The backbone of our cookie cups!
• 1 ½ teaspoons baking powder: Our trusty leavening agent for perfectly puffed cookies.
• ½ teaspoon salt: Balances the sweetness and brings out all those wonderful flavors.
• ¼ teaspoon ground nutmeg (Optional): Adds a lovely hint of warmth to the cookie dough, especially nice with pumpkin.
• ½ cup unsalted butter, softened: Room temperature butter is key for a smooth, creamy cookie dough.
• 1 cup white sugar: For that essential cookie sweetness.
• 1 egg: Acts as a binder and adds richness to our cookie dough.
• 2 tablespoons milk: A little moisture to bring the dough together beautifully.
• 1 (3 ounce) package cream cheese, softened: The secret to our unbelievably creamy and tangy filling! Make sure it’s nice and soft.
• 1 cup confectioners’ sugar, divided: This sweetens our cream cheese base.
• ⅓ cup pumpkin puree: The star of the show! Be sure to grab 100% pumpkin puree, not pumpkin pie filling.
• 2 ¾ cups confectioners’ sugar: For the main part of our luscious, sweet pumpkin filling.
• 1 ½ teaspoons ground cinnamon: The quintessential fall spice!
• ¼ teaspoon ground nutmeg (Optional): Double the nutmeg, double the fall flavor!
• ¼ teaspoon ground ginger: Adds a lovely zing and depth to the spice blend.
• 1 pinch ground cloves: Just a tiny touch for that authentic, cozy pumpkin spice aroma.

How to Make Dianne’s Pumpkin Cookie Cups

1. Preheat Oven & Grease Muffin Cups: First things first, let’s get your oven ready! Preheat it to a cozy 400°F (200°C). Then, grab your miniature muffin tin – you’ll need about 32 cups – and give them a good grease. This ensures our little cookie cups pop right out with no fuss.

2. Sift Dry Ingredients: In a medium bowl, sift together your all-purpose flour, baking powder, salt, and that optional (but highly recommended!) ¼ teaspoon of ground nutmeg. Sifting helps ensure everything is perfectly combined and gives your cookies a lighter texture.

3. Cream Wet Ingredients: Now, in a separate, larger mixing bowl, get out your electric mixer. Cream together that softened unsalted butter with the white sugar until it’s wonderfully smooth and fluffy. Next, beat in the egg and the milk, making sure everything is well incorporated.

4. Combine Wet and Dry: Reduce your mixer speed to low. Gradually add the dry flour mixture to your wet ingredients. Mix just until the dough comes together. Be careful not to overmix here – too much mixing can lead to tough cookies, and we want them tender!

5. Form Cookie Balls: Time to get your hands a little messy – in the best way! Pinch off tablespoonfuls of dough, roll them into neat little balls, and gently place them into each prepared mini muffin cup.

6. Bake the Cookie Cups: Pop your muffin tin into the preheated oven. Bake for about 8 to 10 minutes, or until the edges of the cookies just start to turn a beautiful golden brown. Keep an eye on them; mini cookies bake fast!

7. Initial Cool & Press: Once baked, take them out of the oven and let them sit in the pan for just 1 minute. This brief rest helps them set up a little. Now for the ‘cup’ part! Using the back of a rounded teaspoon (or even your clean thumb!), gently press a small depression into the top of each warm cookie. This creates the perfect little well for our delicious pumpkin filling.

8. Final Cool: Let the cookies cool in the pan for another 5 minutes before carefully removing them to a wire rack to cool completely. Give them a gentle twist as you lift them out to help them release easily. Don’t rush this step; completely cooled cookies are essential before adding the filling!

9. Make Cream Cheese Base: While your cookie cups are cooling, let’s make that dreamy filling! In a clean bowl, beat the softened cream cheese with 1 cup of confectioners’ sugar using your electric mixer until it’s super smooth and lump-free.

10. Add Pumpkin Puree: Slowly beat in the pumpkin puree until it’s thoroughly combined with the cream cheese mixture. It’ll start to look wonderfully orange and creamy!

11. Sweeten the Filling: Gradually beat in the remaining 2 ¾ cups of confectioners’ sugar, a little at a time, until the filling is thick and luscious. Taste it and adjust if you like it sweeter!

12. Spice it Up: Finally, stir in your cinnamon, the remaining ¼ teaspoon of nutmeg, ¼ teaspoon of ginger, and that tiny pinch of ground cloves. This spice blend will make your filling absolutely irresistible and give it that quintessential fall flavor.

13. Fill the Cookie Cups: Once your cookie cups are completely cool, spoon or pipe the glorious pumpkin mixture into each depression. If you’re using a piping bag, you can get really fancy with it! If not, a small spoon works perfectly. And there you have it – beautiful, delicious Dianne’s Pumpkin Cookie Cups, ready to be devoured!

Substitutions & Additions

Feel free to get creative with these cookie cups!

• Spice Blends: If you don’t have all the individual spices on hand, you can easily use about 1 ½ teaspoons of pumpkin pie spice blend instead of the cinnamon, ginger, cloves, and the second nutmeg measurement for the filling.
• Citrus Zest: A tiny bit of orange or lemon zest (about ¼ teaspoon) can be added to the cookie dough or the filling to brighten up the flavors beautifully.
• Chocolate Chips: Love chocolate and pumpkin together? Stir a handful of mini chocolate chips into the cookie dough before rolling for a delightful pumpkin chocolate chip cookie cup – much like our popular chocolate chip pumpkin cookies!
• Toppings: Before serving, sprinkle with a dusting of extra cinnamon, coarse sugar, or even a tiny dollop of whipped cream for an extra special touch.
• Glaze Drizzle: For an additional layer of sweetness, you can drizzle the tops with a simple vanilla glaze made from confectioners’ sugar and a splash of milk.

Tips for Success

• Room Temperature Ingredients: This is a golden rule for baking! Ensure your butter, egg, milk, and especially your cream cheese are at room temperature. It makes creaming and mixing so much smoother and prevents a lumpy filling.
• Don’t Overmix the Dough: Once you add the flour mixture, mix just until the dough comes together. Overmixing develops the gluten in the flour, leading to tough, chewy cookies, and we want them tender and delicate.
• Accurate Pumpkin Puree: Always double-check that you’re using 100% pumpkin puree, not pumpkin pie filling. Pie filling has added sugars and spices that will throw off the flavor balance and texture of your recipe.
• Cool Completely: Patience is a virtue here! Resist the urge to fill warm cookie cups. The creamy filling will melt and slide right off if the cookies aren’t completely cool.
• Gentle Press: When making the depression, be gentle but firm enough to create a nice, deep well for the filling without breaking through the bottom of the cookie.
• Make Ahead Magic: You can bake the cookie cups a day or two in advance and store them in an airtight container at room temperature. Make the filling the day you plan to serve and fill just before guests arrive for ultimate freshness. This strategy also works wonderfully for other baked goods, like preparing blueberry pie bombs ahead of time for a quick dessert. The filling itself can also be made a day ahead and stored in the fridge.

How to Store Dianne’s Pumpkin Cookie Cups

Once filled, Dianne’s Pumpkin Cookie Cups are best stored in an airtight container in the refrigerator. They’ll stay fresh and delicious for up to 3-4 days. For best flavor, I recommend letting them come to room temperature for about 15-20 minutes before serving, as this really brings out their soft texture and creamy filling.

FAQs

Can I use pumpkin pie filling instead of pumpkin puree?

No, I don’t recommend it for this recipe. Pumpkin pie filling already has sugar and spices added, which would make your cookie cups overly sweet and throw off the balance of flavors and consistency. Stick with 100% pumpkin puree!

Can I make these cookie cups in a regular-sized muffin tin?

You can, but you’ll get fewer, larger cookies and the baking time will need to be adjusted. Start with about 12-15 minutes and watch them closely. The proportions of cookie to filling might also feel a little different, but they’ll still be super tasty!

How do I get the filling into the cups neatly without a piping bag?

No fancy piping bag? No problem! A small spoon works perfectly. For a slightly neater look, you can spoon the filling into a Ziploc bag, snip off one corner (about ½ inch wide), and pipe it into the depressions that way. It’s an easy kitchen hack!

Can I freeze these pumpkin cookie cups?

Yes, you can! I’d recommend freezing the unfilled cookie cups in an airtight container for up to 2-3 months. Thaw them at room temperature, then prepare the filling and assemble as usual. The filling itself can also be frozen, but sometimes cream cheese-based fillings can separate slightly upon thawing. If you freeze the filling, let it thaw in the fridge and give it a good whisk to re-emulsify before using.

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