Preheat your oven to 350°F. Line baking sheets with parchment paper.
Beat the softened butter and powdered sugar until light and fluffy, about 2–3 minutes.
1 cup unsalted butter, 0.75 cup powdered sugar
Stir in the vanilla extract until fragrant.
1 teaspoon vanilla extract
Gradually mix in the flour and salt until the dough holds together.
2 cups all-purpose flour, 0.5 teaspoon salt
Fold in the drained, chopped cherries.
10 ounces maraschino cherries
Scoop dough with a 1-inch cookie scoop onto sheets, spacing 2 inches apart.
Bake for 12–14 minutes, until edges are lightly golden.
Let cookies rest on the sheet for 5 minutes, then transfer to a wire rack to cool completely.
Melt the chocolate in a microwave-safe bowl in 30-second intervals until smooth.
8 ounces semi-sweet chocolate
Dip each cooled cookie into the melted chocolate and return to parchment. Let set at room temperature for 15–20 minutes.
8 ounces semi-sweet chocolate