Start by preheating your oven to 350°F. Go ahead and line your baking sheets with parchment paper to help with clean up later, and set them aside.
In a large mixing bowl, cream your softened butter and sugar together until it’s light and fluffy.
Next, you’ll want to add your milk, egg, and vanilla extract to your sugar mixture. Mix this until it’s thoroughly combined.
In a separate smaller bowl, mix the flour, cocoa powder, and salt together.
Slowly add these ingredients into the butter mixture until the cookie dough forms.
Take your chocolate cookie dough and shape it into 1 inch balls. Place them gently on your lined baking sheet we set aside earlier.
In the center of each cookie, press down slightly to create a small dent where your cherry will go. This dent should be about an inch wide.
Place a maraschino cherry in the center of the dent in each chocolate cookie.
Bake your chocolate cherry cookies for 9 to 11 minutes and then allow them to cool completely.