Chocolate Cherry Thumbprint Cookies: A Rich, Fudgy, and Festive Bite

These Chocolate Cherry Thumbprint Cookies are the elegant, bite-sized dessert your holiday table desires. Imagine a rich, tender, and fudgy chocolate shortbread cookie, its center cradling a dollop of glossy, sweet-tart cherry jam that glistens like a jewel. Each cookie is a perfect two-bite balance of deep, dark chocolate and bright, fruity cherry, finished with a delicate drizzle of chocolate for a truly professional touch.

They are surprisingly simple to make, yet their stunning appearance and sophisticated flavor make them look like they came from the finest bakery.

WHY YOU WILL LOVE THESE CHOCOLATE CHERRY THUMBPRINT COOKIES

You will be completely charmed by these delightful Chocolate Cherry Thumbprint Cookies for so many reasons.

• Firstly, these Chocolate Cherry Thumbprint Cookies offer the most satisfying contrast in texture and flavor, the crumbly, melt-in-your-mouth chocolate cookie against the soft, sticky-sweet cherry filling.
• Secondly, they are incredibly fun and simple to make; pressing the thumbprint is a task loved by bakers of all ages.
• Furthermore, they are incredibly versatile and perfect for gifting, stacking beautifully in a tin or box.
• Finally, they are a guaranteed crowd-pleaser, offering a more sophisticated twist on the classic thumbprint cookie that will impress every guest.

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WHAT YOU WILL NEED

The ingredient list is straightforward, with quality cocoa powder making all the difference.

For the Chocolate Shortbread Dough:

• All-Purpose Flour: The base structure.
• Unsweetened Cocoa Powder: Use Dutch-process cocoa for a richer, darker flavor and color.
• Cornstarch: The secret ingredient! It gives the cookies an irresistibly tender, melt-in-your-mouth, shortbread-like texture.
• Salt: To balance the sweetness.
• Unsalted Butter: One cup (two sticks), softened to room temperature. This is key for a tender crumb.
• Powdered Sugar: Using powdered sugar instead of granulated creates a finer, more delicate texture.
• Vanilla Extract: For warmth.
• Optional: Espresso Powder: A pinch (1/4 tsp) to deepen the chocolate flavor without adding coffee taste.

For the Filling & Drizzle:

• Cherry Jam or Preserves: Use a high-quality jam with good cherry flavor. A seeded jam like Bonne Maman works beautifully.
• Semi-Sweet or Dark Chocolate: For the optional but recommended drizzle.

TOOLS YOU WILL WANT

You will need a stand mixer or electric hand mixer, a medium bowl, a small bowl for the jam, a baking sheet, parchment paper, a teaspoon or small spoon, and a piping bag or zip-top bag for drizzling.

HOW TO MAKE THESE CHOCOLATE CHERRY THUMBPRINT COOKIES

Follow these Chocolate Cherry Thumbprint Cookies steps for perfectly shaped, non-cracking thumbprint cookies.

Make the Chocolate Dough

1. First, in a medium bowl, whisk together the flour, cocoa powder, cornstarch, and salt. Set this aside.
2. Then, in the bowl of your stand mixer fitted with the paddle attachment, cream the softened butter and powdered sugar together on medium speed for 2-3 minutes, until light and fluffy.
3. Beat in the vanilla extract (and espresso powder, if using) until combined.
4. With the mixer on low speed, gradually add the dry ingredients, mixing until the dough just comes together and forms a cohesive ball.

Chill the Dough

1. Form the dough into a disk, wrap it tightly in plastic wrap, and refrigerate for at least 1 hour.
2. This chilling step is crucial! It firms up the butter, making the dough easier to roll and preventing the cookies from spreading too much in the oven.

Shape and Create the Thumbprint

1. Preheat your oven to 350°F (175°C). Line a baking sheet with parchment paper.
2. Scoop the dough into 1-inch balls (about 1 tablespoon each). Roll them between your palms until smooth.
3. Place the balls about 1.5 inches apart on your prepared baking sheet.
4. Using your thumb, the back of a 1/4 teaspoon measuring spoon, or the end of a wooden spoon, gently press a deep indentation into the center of each dough ball. Don’t press all the way through to the baking sheet.

Bake and Fill

1. Bake the cookies for 10-12 minutes. They will look set but still soft.
2. As soon as you remove the baking sheet from the oven, gently re-press the indentations with the back of the spoon (they puff up a little while baking).
3. Carefully spoon about 1/2 teaspoon of cherry jam into each warm indentation. The warmth of the cookie will help the jam settle.
4. Let the cookies cool on the baking sheet for 5 minutes before transferring them to a wire rack to cool completely.

Add the Chocolate Drizzle

1. Once the cookies are completely cool, melt the chocolate in a microwave-safe bowl or over a double boiler.
2. Transfer the melted chocolate to a small piping bag or a zip-top bag with a tiny corner snipped off.
3. Drizzle the chocolate in fine lines over the cookies. Let the chocolate set at room temperature or in the refrigerator.

TIPS AND TRICKS FOR PERFECT CHOCOLATE CHERRY THUMBPRINT COOKIES

I want to share my best tips to make your Chocolate Cherry Thumbprint Cookies flawless. To prevent the dough from cracking when you press the thumbprint, you can slightly wet your thumb or the spoon. Furthermore, if your jam is very thick or chunky, you can warm it slightly in the microwave for 10 seconds to make it easier to spoon.

For the cleanest thumbprints, chill the shaped dough balls on the baking sheet for 10-15 minutes before baking. The cornstarch is non-negotiable for that signature tender, sandy shortbread texture. Do not skip it!

VARIATIONS YOU WILL ACTUALLY TRY

This Chocolate Cherry Thumbprint Cookies recipe is a fantastic canvas for creativity. For a Chocolate Orange Thumbprint, add the zest of one orange to the dough and fill with orange marmalade. For a Peppermint Patty version, fill the thumbprint with a small piece of soft peppermint patty or a mint chocolate kiss after baking. You can also roll the dough balls in finely chopped pecans or walnuts before baking for a nutty crunch.

MAKE-AHEAD, STORAGE & FREEZING

These Chocolate Cherry Thumbprint Cookies are a holiday baking lifesaver. You can store the fully cooled and drizzled cookies in a single layer in an airtight container at room temperature for up to 5 days. They freeze beautifully! Freeze the baked, unfilled cookies, then fill with jam and drizzle after thawing. You can also freeze the shaped dough balls and bake directly from frozen, adding 1-2 minutes to the baking time.

TROUBLESHOOTING: COMMON QUESTIONS

Let’s solve any potential issues.

• If my cookies spread too much, the dough likely wasn’t chilled long enough, or your butter was too soft.
• If the thumbprint fills in during baking, your indentations weren’t deep enough, or you need to re-press them immediately after baking.
• If the jam bubbles over, you may have overfilled the indentations; a little goes a long way! Can I use a different jam? Absolutely! Raspberry, apricot, or even a spicy pepper jelly would be fantastic.

SERVING SUGGESTIONS

These Chocolate Cherry Thumbprint Cookies are elegant enough to serve on a tiered stand at a holiday party. They pair perfectly with a glass of port, a cup of espresso, or a glass of cold milk. For gifting, place them in small parchment-lined boxes or tins; they are a heartfelt, homemade present anyone would adore.

NUTRITION NOTES

This is a rich, buttery treat. For a slightly lighter version, you cannot reduce the butter, but you can use a sugar-free jam for the filling.

MY STORY: WHY I ADORE THESE COOKIES

These Chocolate Cherry Thumbprint Cookies are my modern twist on a childhood favorite. My grandmother made classic jam thumbprints every Christmas, and I loved being her official “thumbprint presser.” When I grew older and my taste turned to darker, richer flavors, I wondered what her cookie would be like if it wore a little black dress.

This Chocolate Cherry Thumbprint Cookies version was the delicious answer. Now, I make them every year, and the act of pressing my thumb into the dark dough still connects me to those sweet, flour-dusted afternoons in her kitchen. They are tradition, reinvented.

FINAL CHECKLIST BEFORE YOU BAKE

Before you start, do a quick scan:

• Butter is softened but still cool.
• Dough has chilled for at least 1 hour.
• Oven is preheated to 350°F (175°C).
• Baking sheet is lined with parchment.
• Your jam is ready to spoon.

CHOCOLATE CHERRY THUMBPRINT COOKIES FAQS