These Chocolate Covered Strawberry Cookie Cups are a chocolate cake mix cookie that is filled with homemade strawberry buttercream and topped with a chocolate covered strawberry.  They are perfect for Heart Day or ANY day.

When I think of a Valentine’s Day dessert my mind always goes to chocolate covered strawberries.  They are wonderful and the best part is that they are easy to make.  You literally only need 2 ingredients and about 15 minutes but you know that I couldn’t stop there.  I had to figure out how to add them to a cookie because…why not!? 

Thinking of new ideas for cookies is one of my biggest hobbies.  I especially love cookie cups because it allows me to fill them with something delicious, like I did in these Black Forest Cookie Cups.

In this case I took a basic buttercream and added strawberry jam for the perfect combination.  This strawberry buttercream is AMAZING.  

In fact, I am using it again this weekend to make another Valentine treat that I can’t wait to share.

But it is the addition of the chocolate covered strawberry that really takes this cookie over the top in the best way possible. They’re the reason my Chocolate Covered Strawberry Cake is such a hit, after all! 

I just know you are going to love these Chocolate Covered Strawberry Cookie Cups just as much as I do.

How to Make Chocolate Covered Strawberry Cookie Cups

1. The base for this cookie is made with a chocolate cake mix which means that it is super easy. Combine the cake mix, eggs and oil in a medium bowl and mix with a hand held mixer {or by hand} until everything is combined. The dough will be thick and sticky which is exactly what you want.
2. To get the cookie to bake into a cup we are going to use a mini muffin pan to bake the cookies in. Use a small cookie scoop and scoop mounds of dough into a mini muffin pan that has been liberally sprayed with non stick spray.

3. Then go back and use your fingers to press the dough down so that it flat. Bake the cookies in a 350 degree oven for 9-11 minutes.
4. Once you remove them from the oven, immediately take a knife or offset spatula and run it around the edges of each cookie to loosen it up. If you wait too long, they will not release from the pan well.  I have found that doing this immediately from the oven works best.  Then allow the cookies to cool for a few minutes in the pan.

5. After a few minutes, use a tart shaper {or the end of a spoon} to make an indention into the top of each cookie cup. This will be the vessel for our wonderful filling.
6. While the cookies are cooling completely, turn your attention to making your easy chocolate covered strawberries. Start by melting the chocolate wafers in the microwave.  Begin with 1 minute, stir and then add 30 second intervals until the chocolate is completely melted and smooth.

7. I normally hold the top of the strawberry by the green stem but you could also put a tooth pick in the center. Dip each strawberry into the melted chocolate and then shake it just a bit to remove any extra chocolate.  Place them onto a parchment or wax paper lined baking sheet.
8. After I had dipped all of the strawberries I went back through and added a chocolate drizzle to the top of each strawberry but it isn’t necessary. Allow the strawberries to sit at room temperature until the chocolate is set or place them in the refrigerator if you want the process to happen faster.

9. The final step is to make the strawberry buttercream with strawberry jam.  Begin by combining the softened butter and powdered sugar in a medium bowl with a hand held {or stand} mixer. Once combined add the strawberry jam and continue to mix until creamy and smooth. 
10. To assemble your strawberry cookie cups, place all of the cookie cups onto a cookie sheet. Place the strawberry buttercream in a piping bag {or Ziploc bag} and then pipe the filling into each cookie cup.  I used a piping tip but you wouldn’t have to. You could also spoon the buttercream into each cookie if don’t have access to a piping bag.

11. The last step of assembly is adding a chocolate covered strawberry.  Place it on top of the strawberry buttercream.

Expert Tips

• Liberally spray non stick spray in the mini muffin pan, so that the cookies will easily release.
• Don’t over bake the cookie cups {or any of my other chocolate cake mix cookie recipes} or they won’t be soft enough to make the indention.
• Use a knife or offset spatula to run around each cookie as soon as you remove them from the oven to release the cookie.
• Make the indention in each cookie with a tart shaper {or end of a spoon} while the cookies are still partially warm. I used this same technique in my Pinata Cookies!
• Let the cookies completely cool before adding the filling.
• If you feel like the butter cream is too stiff then you can thin it with a little milk or cream.
• The buttercream will be a beautiful shade of light pink.  If you want it to be a deeper shade you could always add a bit of food coloring.

Do you love Cookie Cups/Bites?  Try these recipes…

Cake Mix Cookies

Banana Pudding Cookie Cups {made with a Cake Mix}

Cookies

Lemon Bar Cookie Cups Recipe

Cake Mix Cookies

Cannoli Cookie Cups {made with a Cake Mix}