Chocolate and Cherry Thumbprint Cookies are my updated version of a classic! These chewy chocolatey cookies feature tasty cherry pie filling in the center, are then are drizzled with extra melted chocolate on top. Are you drooling yet?! They are just perfect for the cherry-chocolate aficionados in your life. I dare you to try to eat just one!!
Those who know me know that I’ve never met a cookie I don’t like. Seriously!
The dozens of cookie recipes that I have up on the site right now are proof… and to be honest with you I probably have close to 100 at this point!!
My all-time favorites always include chocolate. S’mores Cookies, Triple Chocolate Cookies, Chocolate Cake Mix Cookies, Devil’s Food Cookies… I’ve got something for every taste preference and occasion!
These chocolate cherry thumbprint cookies are the latest addition to my choco-cookie lineup. They’re decadent, flavorful, and look pretty impressive too!
Ingredient Notes and Substitutions
- Sugar – I love using a combination of granulated white sugar and light brown sugar in cookies.
The brown sugar especially will give you soft, chewy, and moist results every time!
- All-Purpose Flour – All-purpose is your best bet for thumbprint cookies. It’s easiest to find and it will give you a tender texture.
- Cocoa Powder – Opt for unsweetened cocoa powder as you’ll get plenty of sweetness from the sugars, chocolate, and cherry pie filling. You don’t want to overdo it!
- Chocolate Chips – I’m using mini semi-sweet chocolate chips for my cherry thumbprint cookies.
I like the minis as they don’t overwhelm the batter!
- Cherry Pie Filling – Store-bought from a can is totally fine! If you’re feeling extra ambitious you could make it yourself, but it really isn’t necessary.
- Chocolate Almond Bark – I love melting down almond bark to use as a drizzle. It’s made with vegetable fat instead of cocoa butter, which means it’s super easy to melt.
Since these are chocolate thumbprint cookies, I had to go for chocolate-flavored bark!
Helpful Tips for Perfect Chocolate Thumbprint Cookies
- The easiest way to create the “thumbprint.”
Thumbprint cookies get their name thanks to the small well in the center of each cookie.
These small indents were originally made by sticking your thumb into the cookie dough before baking.
While you can absolutely feel free to use your thumb, the end of a wooden spoon or spatula is a great alternative!
- Gently fold in the chocolate chips.
When you add the mini chocolate chips to your dough, make sure to fold them in gently.
Overmixing can lead to tough chocolate thumbprint cookies, and I know you don’t want that!
Stop mixing once the chips are incorporated evenly. Nothing more, nothing less!
- Perfecting your chocolate drizzle.
Adding a bit of coconut oil to your chocolate almond bark can make drizzling a lot easier! ⅛ teaspoon is enough.
You could also place the melted almond bark in a Ziploc bag with the tip cut off to make the whole process a lot less messy!
The Best Way to Store Cherry Thumbprint Cookies
When the cookies are cool, store them in an airtight container. If you need to stack the cookies, I recommend placing a sheet of parchment paper between each layer.
Chocolate cherry thumbprint cookies will last for 3-5 days at room temperature. You can extend their shelf life to about a week if you keep them in the fridge.
Kitchen Tools You Will Need
- Baking Sheets lined with parchment paper – Used for anything from cookies to roasting, a good baking pan will last for years.
- Mixing Bowls – I like to have a variety of sizes on hand, and this set has them all.
- Whisk – These have held up for over 10 years and are still as good as the day I bought them. With 3 sizes, there is a whisk for every job!
- Wooden Spoon – Use this to create your thumbprint!
- Microwave-Safe Bowl – Not only does it make melting chocolate easier, but you can use it to quickly steam vegetables too!
Chocolate Cherry Thumbprint Cookies FAQ
You most likely overmixed the dough, or it could be that you didn’t shape the cookie dough balls correctly. Pressing too hard when you make your thumbprint can also cause them to fall apart!
Make sure to let your cherry thumbprint cookies cool for at least 10 minutes on the baking sheet — that extra time helps them set and hold their shape!
Butter is a fat, and when that fat melts and there isn’t enough flour to hold it together, your cherry thumbprint cookies will spread as they bake.
Pay close attention to the quantities that are indicated on the recipe card when measuring out your ingredients!
You sure can! I recommend freezing after baking.
Allow them to cool completely before flash-freezing them. When they’re firm, place them in an airtight container and store in the freezer for up to 2-3 months.
When you’re ready to enjoy, let the chocolate thumbprint cookies thaw and then reheat them in the oven for a few minutes if you’d like.
With love, from our simple kitchen to yours.
Other Delicious Cookie Recipes
Thumbprint Cookies (Chocolate Cherry)
- 1/2 cup unsalted butter, softened
- 3/4 cup granulated sugar
- 3/4 cup packed light brown sugar
- 2 large eggs
- 2 teaspoons pure vanilla extract
- 2 1/2 cups all-purpose flour
- 1/2 cup unsweetened cocoa powder
- 1 1/2 teaspoon baking powder
- 1/2 teaspoon salt
- 1 cup semi-sweet mini chocolate chips
- 10.5 ounces cherry pie filling, about half a 21 ounce can
- 6 ounces of chocolate almond bark
- Preheat the oven to 350 degrees and line a baking sheet with parchment paper.
- In a large bowl, combine butter, granulated sugar, and brown sugar.
- Beat in eggs one at a time then add the vanilla.
- In a small bowl, combine unbleached flour, cocoa powder, baking powder, and salt.
- Mix dry ingredients into the wet ingredients. Dough will be thick and crumbly. You may have to use your hands to get it to come together.
- Fold in semi-sweet mini chocolate chips.
- Using a 1 tablespoon cookie scoop, create cookie balls and place them 1” apart on the baking sheet.
- Use the end of a large baking spoon or spatula to create a hole in the middle of each cookie.
- Put some pie filling in each hole and then top with one cherry.
- Bake for 10-11 minutes. Cookies will look set and will continue baking on the baking sheet (do not over bake).
- Remove from the oven and let cool on the baking sheet.
- While cooling, heat chocolate almond bark in a microwave safe bowl in 20-30 second increments until melted completely (stirring between each).
- Drizzle chocolate over cherry thumbprint cookies and let cool completely.
All nutritional information is based on third party calculations and is only an estimate. Each recipe’s nutritional value will vary depending on the ingredients used, measuring methods, and portion sizes.
Originally published November 2023
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