1. Prepare the Baking Trays and Oven

Start by preheating your oven to 350 degrees Fahrenheit. Line two baking sheets with parchment paper to prevent sticking and to help the cookies bake evenly.

Preparing the trays ahead of time is important because the dough comes together quickly once the wet and dry ingredients are combined. Parchment paper also helps create softer bottoms while keeping cleanup easy.

Before beginning the dough, drain the maraschino cherries thoroughly. Pat them dry with paper towels. Removing excess moisture prevents the cherries from making the cookie centers soggy during baking.

2. Melt the Chocolate Chips

Place the semisweet chocolate chips into a microwave safe bowl. Microwave in short intervals, stirring every 20 to 30 seconds until smooth and melted.

Allow the melted chocolate to cool slightly before adding it to the dough. Warm chocolate blends more evenly with the butter mixture and helps create a rich chocolate flavor throughout the cookies.

This melted chocolate gives the cookies a fudgy texture that pairs beautifully with the cocoa powder. Using both melted chocolate and cocoa powder creates a deeper, more intense flavor than using cocoa alone.

3. Combine the Dry Ingredients

In a medium mixing bowl, whisk together the quick cooking oats, all purpose flour, cocoa powder, baking soda, baking powder, and salt.

Whisking the dry ingredients separately ensures the leavening agents are evenly distributed throughout the dough. This helps the cookies bake consistently and keeps the texture uniform.

The oats add subtle chewiness and body to the cookies. Even though the cookies are chocolate based, the oats provide a pleasant texture that keeps them from feeling overly dense.

4. Cream the Butter and Sugar

In a large bowl, beat the softened butter and granulated sugar together until light and creamy. This process usually takes about 2 to 3 minutes with an electric mixer.

Creaming properly creates a lighter texture and helps incorporate air into the dough. The butter should be soft enough to mix easily but not melted.

Once the mixture looks fluffy, add the eggs one at a time, mixing well after each addition. Stir in the vanilla extract.

The eggs help bind the dough together while also adding richness. Vanilla enhances the chocolate flavor and gives the cookies a warm bakery style aroma.

5. Add the Melted Chocolate

Pour the cooled melted chocolate into the butter mixture and mix until fully incorporated.

At this stage, the dough becomes glossy, thick, and deeply chocolatey. Make sure to scrape down the sides of the bowl so everything mixes evenly.

The melted chocolate is what gives these cookies their rich brownie like quality. It also creates a smooth texture that balances beautifully with the oats.

6. Mix the Wet and Dry Ingredients Together

Gradually add the dry ingredient mixture into the wet ingredients. Stir until everything is fully combined and no dry streaks remain.

The dough will be thick and slightly sticky. Avoid overmixing because excessive mixing can make the cookies tough.

Once combined, cover the bowl and refrigerate the dough for about one hour. Chilling the dough helps the cookies hold their shape during baking and intensifies the flavor.

Cold dough also makes shaping the cookies much easier.

7. Shape the Cookies

Once chilled, scoop portions of dough and roll them into evenly sized balls. Arrange them on the prepared baking sheets, leaving space between each cookie.

Using your thumb or the back of a rounded spoon, create an indentation in the center of each cookie.

The indent should be deep enough to hold the cherry securely without flattening the cookie completely.

If the dough cracks slightly around the edges while shaping, gently smooth it back together using your fingers.

8. Add the Maraschino Cherries

Place one maraschino cherry into the center indentation of each cookie.

Press gently so the cherry stays in place while baking. The bright red cherries create a beautiful contrast against the dark chocolate dough and give the cookies their signature appearance.

The sweetness of the cherries balances the rich cocoa flavor perfectly. Their soft texture also adds a juicy element to every bite.

9. Bake the Cookies

Bake the cookies for 10 to 12 minutes or until the edges are set.

The centers may still look slightly soft when removed from the oven, but they will continue to firm up as the cookies cool.

Avoid overbaking because these cookies are meant to stay soft and fudgy in the center.

Let the cookies cool on the baking sheet for about 2 minutes before transferring them to a wire rack.

Cooling gradually helps the cookies maintain their shape while finishing the baking process internally.

10. Cool and Serve

Allow the cookies to cool completely before serving.

As they cool, the chocolate flavor deepens and the texture becomes perfectly soft and chewy. These cookies taste wonderful slightly warm, but they are even better once fully set.

Serve them with coffee, hot chocolate, or cold milk for a comforting dessert experience.

The cookies can also be stored in an airtight container for several days while maintaining their soft texture.