Set the oven to 350°F and let it preheat before baking. The oven should reach the full temperature before the filled dough portions go in.

Beat the butter with the sugar in a large mixing bowl, then incorporate the egg and vanilla. Look for a fluffy, evenly blended butter mixture first, followed by a smooth mixture after the egg goes in.

Gradually beat the flour, sifted cocoa, baking powder, baking soda, and salt into the butter mixture until incorporated. Expect a dry-looking dough with an almost crumbly texture, rather than a loose or sticky consistency.

Portion the dough with a cookie scoop into 1-tablespoon balls, coat them in sanding sugar or white granulated sugar, and arrange them on a parchment-lined cookie sheet. Use the tablespoon measure as your guide because scoop numbering can vary by manufacturer.

Collect the cherry juice as you drain the jar, blot the cherries thoroughly dry, halve any extra-large fruit, and press a cherry firmly into each dough ball. The fruit should sit securely in a deep indentation without breaking through the dough underneath.

Bake at 350°F for 10–12 minutes, then remove the sheet and give the cookies 5 minutes to cool before frosting them warm. The cookies should look set when they leave the oven, with dough holding its shape around each cherry.

During baking, bring the cream just to a simmer, pour it over the chocolate chips, wait 3 to 5 minutes, stir gently until smooth, and blend in 1 tablespoon of reserved cherry juice. The chocolate should melt into a uniform mixture before the juice is added, without visible streaks of cream.

Let the ganache cool slightly and thicken, then spoon 1–2 teaspoons over each warm cookie to cover the cherry, adding sugar or decorations if desired. The topping should mound softly over the fruit instead of immediately flowing onto the parchment.