Mastering the Art of Stuffed Pumpkin Spice Kiss Cookies: Your Ultimate Guide

There’s a special joy that comes with the changing seasons, and for many of us, that joy is inextricably linked with holiday candy. As a self-proclaimed holiday candy enthusiast, I find myself drawn to those special, limited-edition flavors that pop up for just a short time each year. Hershey Kisses, with their myriad seasonal varieties, are a particular favorite. This past fall, the Candy Corn White Chocolate M&Ms were a delightful surprise, but it was the Pumpkin Spice Kisses that truly captured my imagination.
While simply enjoying candy straight from the bag has its merits, my true passion lies in transforming these seasonal treasures into something even more magical. This year, I knew these delightful pumpkin spice morsels were destined for a batch of cookies. My initial thought gravitated towards classic “blossom” cookies, where the kiss sits atop a soft cookie. However, I decided to elevate the experience, creating these truly special Stuffed Pumpkin Spice Kiss Cookies. There’s something undeniably satisfying about biting into a rich chocolate spice cookie to discover a hidden pumpkin spice delight within.
My journey with kiss cookies hasn’t always been smooth. Years ago, a friend and I attempted a similar recipe, and the outcome was, to put it mildly, a disaster. We ended up with a sticky, shapeless mess that barely resembled a cookie. At the time, I blamed the recipe, not fully understanding the nuances of baking. Perhaps we used the wrong type of fat, or more likely, we failed to properly encase the delicate kisses. Fast forward to last weekend, and with significantly improved baking skills and a dash of determination, I decided it was time for a redemption. And what a delicious redemption it turned out to be!
The Irresistible Flavor Trio: Chocolate, Cinnamon, and Clove

If there’s one flavor combination that truly embodies autumn, it’s the harmonious blend of cinnamon and clove. For me, these two spices are inseparable; where there’s one, the other must follow. When you introduce the rich, comforting depth of chocolate to this duo, you unlock an absolutely incredible trio of flavors that perfectly complements the pumpkin spice notes of the hidden kiss. Seriously, if you’ve never considered it, try adding a pinch of both cinnamon and clove to your next batch of chocolate chip pancakes. The warmth and complexity they bring are transformative, and I promise, you’ll thank me for the suggestion!
In these Stuffed Pumpkin Spice Kiss Cookies, this spice and chocolate blend forms the perfect cocoon for the sweet, seasonal kiss. The chocolate cookie dough, subtly spiced with cinnamon and clove, provides a robust base that enhances the delicate pumpkin spice flavor of the filling without overpowering it. It’s a symphony of fall flavors in every single bite.
A Melt-in-Your-Mouth Texture That Surprises

Beyond the exquisite flavor, the texture of these cookies is truly something to rave about. I was genuinely surprised by their delicate, melt-in-your-mouth quality, reminiscent of a fine shortbread. Expecting just an “average” cookie, I was delighted by how tender and crumbly they became after baking. This delicate nature does mean they require a bit of careful handling. I found that baking them a few minutes longer than initially directed was beneficial, allowing them to firm up just enough to be gently removed from the cookie sheet without crumbling. Patience in cooling is also key for maintaining their perfect shape and structure.
The Unexpected Orange Delight Within

Another delightful surprise came when I unwrapped the Pumpkin Spice Kisses themselves. I had anticipated a standard chocolate kiss with a pumpkin-flavored cream filling, but instead, I was greeted by a vibrant orange chocolate! This unexpected burst of color adds a fantastic visual element to the cookie. When you bite into one of these chocolate spice treasures, the bright orange kiss nestled in the center creates a beautiful and inviting contrast, making each cookie not only a treat for the taste buds but also a feast for the eyes. It’s these small details that truly elevate a simple cookie to something memorable and special, perfect for sharing during fall gatherings or cozy evenings.
Versatility: Beyond Just Pumpkin Spice Kisses

While the Pumpkin Spice Kisses (which I’ve readily found at major retailers like Walmart and Target during the fall season) are undeniably perfect for these cookies, don’t let their seasonal availability limit your baking ambitions! This recipe is incredibly versatile and can be adapted to any variety of Hershey’s Kisses you desire. Whether you opt for the classic milk chocolate, the rich caramel-filled, creamy Hugs, nutty almond, or even the airy aerated versions, pretty much whatever your local grocery store has in stock will work wonderfully.
Think seasonally! As winter approaches, you could easily swap in festive mint or cherry kisses for a completely different holiday vibe. There’s also a “Cookies ‘n’ Creme” kiss available at various times of the year (I believe it’s often seen around Easter, but keep an eye out!). Each different kiss flavor will impart its own unique character to the cookie, making this a recipe you can truly enjoy year-round by simply switching out the star ingredient. Experiment with your favorites and discover a whole new world of stuffed cookie possibilities!
Why These Stuffed Pumpkin Spice Kiss Cookies Are Your Next Baking Project
These cookies aren’t just a treat; they’re an experience. Here’s why they deserve a spot on your baking list:
- Perfect Autumn Flavor: The blend of chocolate, cinnamon, clove, and pumpkin spice is quintessential fall.
- Irresistible Texture: A delicate, melt-in-your-mouth shortbread-like cookie shell.
- Delightful Surprise Center: Each bite reveals a soft, flavorful pumpkin spice kiss.
- Visually Appealing: The vibrant orange kiss creates a beautiful contrast with the dark chocolate cookie.
- Customizable: Easily adaptable with various Hershey’s Kiss flavors, making them suitable for any season or preference.
- Relatably Easy: With improved skills, this recipe proves that even past baking failures can lead to triumphant results.
Tips for Perfect Stuffed Kiss Cookies Every Time
Achieving these perfect stuffed cookies is simple with a few key tips:
- Chill Your Dough: Don’t skip the chilling step! This firm dough is much easier to work with and helps prevent the cookies from spreading too much during baking. A minimum of one hour is recommended, but you can chill it longer if needed.
- Completely Encase the Kiss: Ensure the Hershey’s Kiss is fully covered by the dough. Any exposed chocolate can melt and ooze out, affecting the cookie’s appearance and texture. Mold the dough carefully around each kiss, making sure there are no cracks or gaps.
- Monitor Baking Time: Ovens vary, so keep a close eye on your cookies. They should be “almost set,” meaning the edges are firm but the centers still look slightly soft. Overbaking can make them dry, while underbaking can make them difficult to handle. If they seem too delicate to remove, bake for an extra minute or two.
- Gentle Removal and Cooling: After baking, let the cookies cool on the parchment-lined cookie sheet for a few minutes. This allows them to firm up before you gently transfer them to a wire rack to cool completely. Handling them too soon can cause them to break.
- Quality Ingredients: Using good quality cocoa powder and fresh spices will significantly enhance the flavor of your cookies.
Creative Variations to Explore
Once you master the basic recipe, feel free to get creative:
- Different Kiss Flavors: As mentioned, any Hershey’s Kiss works! Try Hugs for a creamy white chocolate center, caramel kisses for a gooey surprise, or mint kisses for a festive touch.
- Dough Modifications:
- Nutty Crunch: Add a tablespoon or two of finely chopped pecans or walnuts to the dough for extra texture.
- Spiced Up: Increase the amounts of cinnamon and clove, or introduce other fall spices like nutmeg or ginger for an even bolder flavor profile.
- Citrus Zest: A little orange zest in the chocolate dough could beautifully complement the pumpkin spice flavor.
- Decorative Touches:
- Powdered Sugar Dusting: Once cooled, a light dusting of powdered sugar adds an elegant finish.
- Chocolate Drizzle: A drizzle of melted white or dark chocolate over the cooled cookies can make them even more special.
Storage and Serving Suggestions
- Storage: Store cooled Stuffed Pumpkin Spice Kiss Cookies in an airtight container at room temperature for up to 3-5 days. For longer storage, they can be frozen for up to 2-3 months. Thaw at room temperature before serving.
- Serving: These cookies are perfect with a warm cup of coffee, tea, or a glass of milk. They make an excellent addition to any holiday cookie platter, a thoughtful homemade gift, or a comforting treat on a crisp autumn evening.

Stuffed Pumpkin Spice Kiss Cookies
1 dozen
Delicious chocolate spice cookies with a delightful pumpkin spice kiss hidden inside, perfect for autumn.
Ingredients
- 3/4 cup + 1 Tbsp all-purpose flour
- 2 Tbsp unsweetened cocoa powder
- 1/4 tsp ground cinnamon
- 1/4 tsp ground clove
- Pinch of salt
- 1 stick (1/2 cup) unsalted butter, softened
- 1/3 cup granulated sugar
- 1/2 tsp vanilla extract
- 12 Pumpkin Spice Kisses, unwrapped
Instructions
- In a small bowl, whisk together the flour, cocoa powder, cinnamon, clove, and salt. Set aside.
- In a large bowl, cream together the softened butter, sugar, and vanilla extract until light and fluffy, about 2-3 minutes. Slowly add the whisked flour mixture, mixing until just combined and the dough comes together. Chill the dough for at least 1 hour or until firm enough to handle easily.
- Preheat your oven to 375°F (190°C). Line a cookie sheet with parchment paper. Divide the chilled dough into 12 even balls, each roughly 1 tablespoon in size. Take each dough ball and carefully mold it around one unwrapped Pumpkin Spice Kiss, ensuring the kiss is completely covered. Place the dough-wrapped kisses on the prepared cookie sheet. Bake for 12-14 minutes, or until the cookies are almost set and the edges are slightly firm. Cool on the cookie sheet for a few minutes before gently transferring them to a wire rack to cool completely.
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Source: Adapted from Hershey’s Make It Chocolate