To the bowl of a stand mixer with the paddle attachment, add butter and confectioners' sugar. Mix until fully combined.
With the mixer off, add sweetened condensed milk, coconut, pecans, and vanilla. Mix until all ingredients are well incorporated.
Fold in cherries.
Refrigerate the mixture for at least 3 hours, up to overnight to ensure it firms up and is easier to handle.
When ready, line a baking sheet with parchment paper.
Once the mixture has chilled, remove it from the refrigerator. Using a 1-tablespoon scoop, drop the balls onto the lined baking sheet, rolling each into a ball. Return them to the refrigerator to firm up again while you prepare the chocolate coating. (You may want to keep the candy balls in the refrigerator as you form the rest of them so they don't get too soft.)
When ready, place the semisweet chocolate chips and vegetable oil in a microwave-safe bowl. Heat in 20-second increments, stirring after each interval, until the chocolate is fully melted and smooth. Let the melted chocolate sit for 2 to 2 ½ minutes to cool slightly.
Dip each chilled candy ball into the chocolate, using a spoon to coat it completely. Lift the coated ball out with a fork, allowing any excess chocolate to drip off. Place the dipped candies onto a prepared baking sheet lined with parchment paper.
Top with coconut flakes, if desired.
Let the chocolate coating set before serving.
Store the candies in an airtight container in the refrigerator.