Add ice cream, frozen cherries, milk, malt powder, and vanilla extract to a blender. Tip: For extra cherry flavor, include the optional maraschino cherry juice.

Blend on high until smooth and thick, about 30-45 seconds. Pause to scrape down the sides if needed. Tip: Add a splash more milk if the shake is too thick.

Pour into chilled glasses and serve immediately with a straw and spoon. Tip: Garnish with a fresh cherry or whipped cream for a diner-style touch.