Begin by preheating the oven to 350°F.
Using a stand mixer, cream together the butter and sugars until light in color and fluffy in texture.
Add in the eggs, corn syrup and 1 tbsp of vanilla. Mix until thoroughly combined.
Next, add the flour, cocoa, corn starch, baking soda and salt. Mix until your chocolate cookie dough forms. The dough will be soft.
Divide the dough out into 12 equal portions. I like to use my 1/2 cup measuring cup to help divide the dough, just don’t fill the ½ cup entirely to ensure you have enough dough for 12 cookies.
Roll the cookie dough into a ball and then use your thumb to create a pocket in the middle of the cookie dough.
Spoon approximately 1/2 tbsp of cherry pie filling into each pocket and then close the cookie dough around the pie filling.
Repeat with remaining cookie dough. Place 6 cookies on a cookie sheet lined with parchment paper or a silicone baking mat.
Bake at 350° for 15-17 minutes. The cookie should start to crack and crinkle. You will know it is ready to take out of the oven when it starts to spread slightly and the centers of the cookie no longer look wet.
Allow the cookies to cool completely and then top with chocolate ganache.
To make the chocolate ganache measure out the heavy cream into a microwave-safe bowl.
Microwave the cream for 1 1/2 minutes or until it is boiling.
Remove the bowl from the microwave and add in the chocolate chips. Use a spoon and push the chocolate chips around so they are all covered by the heavy cream.
Allow the chocolate chips to sit in the hot cream for 3 minutes.
After the 3 minutes is up, use a whisk and stir the chocolate chips into the heavy cream until smooth. Spread onto each cookie.
Chill the cookies in the fridge while making the whipped cream frosting.
Make the frosting by adding the heavy whipping cream to either the bowl of your stand mixer or a large bowl that you can use an electric hand mixer with.
Whip the cream on medium-high speed until it starts to thicken.
Once it starts to thicken, slow the speed down and gradually add in the powdered sugar and vanilla. Once all of the powdered sugar has been added, increase the speed to as high as it can go and whip it until stiff peaks form. Once stiff peaks form, the frosting is done!
Add the frosting to a piping bag with a large closed star tip. Pipe a swirl of frosting onto the top of each ganache topped cookie, and then add a cherry and chocolate shavings on top.
Enjoy! Store in the fridge for up to 4 days.