Chocolate Cherry Cookies

When the pans come out of the oven, the cookies are soft and the edges are just set. That’s the moment to press in a shallow well and tuck a cherry into each one; wait until they cool and the tops won’t give as neatly. These Chocolate Cherry Cookies bake up with a tender cocoa center, a bright maraschino cherry, and a spoonful of smooth chocolate on top.

I like how the dough stays soft without turning cakey: butter and sugar are beaten until fluffy, then the dry ingredients go in gradually with the milk. The topping keeps the finish simple, too. Semisweet chocolate and sweetened condensed milk melt into a thick, glossy mixture that settles around each cherry. Let it set before serving, and every cookie has a soft chocolate base with a tidy cherry-chocolate finish.

Why the Cocoa Dough Needs Flour and Milk Added in Turns

Cocoa powder makes this dough behave differently from a plain vanilla cookie dough. It absorbs moisture, so adding all the flour mixture at once can leave a dense-looking mass that’s harder to bring together evenly. The milk helps loosen the dough, but pouring it in all at once can make the mixture look curdled before the flour has incorporated.

Adding the dry mixture in three portions and the milk in two gives the dough time to come together as you mix. Begin and end with the flour mixture, just as you would when alternating ingredients in a cake batter. Once the last bit of flour disappears, stop. Beating beyond that point can develop the flour’s gluten and make the cookies less tender.

The finished dough should be thick enough to scoop, not pour. If you see a small streak of flour, mix briefly until it vanishes; there’s no need to keep beating after the dough looks uniform. That balance is what gives these cookies a soft bite without a heavy, pasty center.

What Gives These Cookies Their Cocoa Base and Cherry-Chocolate Finish

• Unsweetened cocoa powder — It brings the deep chocolate flavor without adding sugar, which matters because the dough and topping are already sweetened. Use cocoa you enjoy the taste of; a fresh, well-sealed container makes a noticeable difference. Keep the unsweetened type here rather than a sweetened cocoa drink mix.
• All-purpose flour and milk — Together, they give the cocoa dough enough structure to hold a cherry while keeping the crumb tender. Regular milk works with the method; add it in the alternating portions rather than pouring it in all at once.
• Unsalted butter — Softened butter creams smoothly with the sugar and helps make the dough light. It should give slightly when pressed, but shouldn’t look melted or greasy. A standard grocery-store butter is fine here.
• Maraschino cherries — Their sweet, syrupy cherry flavor is a good match for the cocoa cookie and the chocolate topping. Choose whole cherries that fit comfortably into the indentation, and drain them well so syrup doesn’t interfere with the topping.
• Semisweet chocolate chips and sweetened condensed milk — The chips supply the chocolate flavor, while condensed milk makes the topping thick enough to spoon over each cherry. Use sweetened condensed milk, not evaporated milk; the latter won’t give you the same sweet, creamy consistency.

How to Bake, Fill, and Top the Cookies Without Losing Their Soft Centers

Get the Butter Mixture Pale and Fluffy

Heat the oven to 350°F and line two large baking sheets with parchment paper. Beat the softened butter and granulated sugar in a large bowl until pale and fluffy, about 2 minutes. Beat in the egg and vanilla until they’re combined. If the butter looks oily rather than creamy, it was too warm to cream properly.

Bring the Cocoa Dough Together Gently

Whisk the flour, unsweetened cocoa powder, baking soda, and salt in a medium bowl. Add that mixture to the butter mixture in three additions, alternating with the milk in two additions; begin and finish with the flour mixture. Mix just until combined, scraping the bowl if a little flour is hiding at the bottom. The dough should look evenly chocolate-colored without dry pockets.

Bake Until the Edges Set, Then Make the Wells

Scoop the dough into 24 portions, about 1 1/2 tablespoons each, and place 12 on each prepared sheet with about 2 inches between them. Bake both sheets for 10–12 minutes, switching and rotating their positions halfway through so they bake evenly. Look for set edges rather than waiting for the centers to look firm. Immediately press a shallow indentation into each cookie with the back of a teaspoon and place a cherry in each one.

Cool the Cookies Before Adding the Topping

Leave the cookies on the baking sheets for 5 minutes, then move them to a wire rack and let them cool completely. The brief rest helps them firm enough to transfer without breaking. Don’t add the chocolate topping while the cookies are still warm; it will soften and spread instead of sitting neatly over the cherries.

Stir the Topping Smooth and Spoon It Over

Put the chocolate chips and sweetened condensed milk in a microwave-safe bowl. Microwave at 50% power in 20-second intervals, stirring after each interval, until the mixture is smooth; then stir in the reserved cherry juice. Spoon about 1 tablespoon over each cherry, guiding the chocolate toward the edges of the indentation. Let the topping set before serving.

Three Ways to Change the Chocolate or Adapt the Dough

Questions That Come Up When Baking Chocolate Cherry Cookies

Chocolate Cherry Cookies

Chocolate cherry cookies pair soft cocoa cookies with a maraschino cherry and a smooth chocolate topping. Bake until the edges are set, then spoon on the warm topping for a glossy finish.

Print Recipe Pin Recipe

Prep Time 20 minutes mins

Cook Time 12 minutes mins

cooling time 5 minutes mins

Total Time 37 minutes mins

Servings: 24 servings

Course: Dessert

Cuisine: American

Calories: 162

Ingredients Equipment Method Notes

Ingredients

  

For the cookie dough

• 0.5 cup unsalted butter softened
• 1 cup granulated sugar
• 1 egg large
• 1 tsp vanilla extract
• 1.5 cup all-purpose flour
• 0.5 cup unsweetened cocoa powder
• 0.5 tsp baking soda
• 0.25 tsp salt
• 0.25 cup milk

For the cherry-chocolate topping

• 24 maraschino cherries drained and patted dry
• 1 tbsp maraschino cherry juice from the jar; reserved
• 1 cup semisweet chocolate chips
• 0.5 cup sweetened condensed milk

Equipment

• 2 large baking sheets
• 1 electric mixer
• 1 microwave

Method

 

Prepare the cookie dough

1. Heat the oven to 350°F.
2. Line two large baking sheets with parchment paper.
3. In a large bowl, beat the butter and sugar until pale and fluffy, about 2 minutes.
4. Beat in the egg and vanilla until combined.
5. In a medium bowl, whisk together the flour, cocoa powder, baking soda, and salt.
6. Add the flour mixture to the butter mixture in three additions, alternating with the milk in two additions and beginning and ending with the flour mixture; mix just until combined.

Bake and fill the cookies

1. Scoop the dough into 24 portions, about 1 1/2 tablespoons each.
2. Arrange 12 portions on each baking sheet, spacing them about 2 inches apart.
3. Bake both sheets for 10–12 minutes, switching and rotating their positions halfway through, until the edges are set.
4. Immediately press a shallow indentation into each cookie with the back of a teaspoon.
5. Place a cherry in each indentation.
6. Let the cookies cool on the baking sheets for 5 minutes.
7. Transfer the cookies to a wire rack and cool completely.

Make the chocolate topping

1. Combine the chocolate chips and sweetened condensed milk in a microwave-safe bowl.
2. Microwave at 50% power in 20-second intervals, stirring each time, until smooth.
3. Stir in the reserved cherry juice.
4. Spoon about 1 tablespoon of the chocolate mixture over each cherry.
5. Let the topping set before serving.

Notes

Pat the cherries thoroughly dry so the chocolate topping settles neatly. Store in an airtight container in the refrigerator for up to 5 days; freezer: yes. For a dairy-free swap, use dairy-free butter, milk, chocolate chips, and sweetened condensed milk.