Drain maraschino cherries thoroughly and finely chop. Use paper towels to press out as much moisture as possible for a firm truffle base.
Beat softened unsalted butter in a large mixing bowl until creamy. Gradually incorporate powdered sugar and vanilla extract, mixing until smooth. Fold in the chopped, dried cherries until the mixture is evenly combined and slightly thick but still pliable.
Scoop about 1 tablespoon of the filling and roll into smooth balls. Place on a parchment-lined baking sheet and freeze for 20–30 minutes, until firm to the touch.
Combine chocolate chips and optional coconut oil or shortening in a microwave-safe bowl. Heat in 30-second intervals, stirring until completely melted and silky.
Using a fork or dipping tool, dip each chilled cherry ball in melted chocolate. Let any excess drip off and return to the parchment-lined tray.
Chill coated truffles in the refrigerator for 15–20 minutes, or until the chocolate is firm and set.
Transfer to an airtight container and refrigerate for up to 1 week. Enjoy chilled or allow to come to room temperature before consuming.