Whisk together the flour and salt in a medium bowl. Set aside.

In a large bowl, beat the softened butter and confectioners' sugar with an electric mixer on medium speed until light and creamy. Beat in vanilla extract.

Gradually add the flour mixture, mixing on low speed. The dough will be crumbly at first—keep mixing until it begins to clump together.

Using a spatula, gently fold in the chopped maraschino cherries and chocolate chips until evenly distributed.

Transfer the dough to a sheet of plastic wrap. Shape into a log about 2 inches in diameter. Wrap tightly and chill for 1–2 hours, or until firm.

Preheat the oven to 325°F (163°C). Line a baking sheet with parchment paper.

Slice the chilled dough log into ¼ to ⅓-inch thick rounds. If any slices crumble, press them back together gently.

Arrange cookies about 1 inch apart on the prepared baking sheet. Bake for 10–15 minutes, until just set and the edges are barely golden (do not overbake).

Cool on the pan for 5 minutes, then transfer to a wire rack to cool completely. Enjoy!