Preheat oven to 375 °F (190 °C). Line baking sheets with parchment paper.

In a large bowl, mix together softened butter, powdered sugar, and vanilla until well blended.

In a separate bowl, whisk together ground almonds, flour, and salt. Combine this dry mix into the butter‑mixture until fully incorporated.

Scoop about one tablespoon of dough and press an indent in the center. Place a halved maraschino cherry inside, then wrap the dough around it to form a ball. Place on prepared baking sheet and slightly flatten.

Bake for 8–9 minutes, or until the edges just start to turn golden. Remove and let cool.

While cookies cool, prepare the frosting: whisk together powdered sugar, reserved cherry juice, and almond extract. Add milk a tablespoon at a time until the mixture reaches a dippable consistency.

Dip the top of each cookie into the frosting, place on a wire rack, and immediately sprinkle red decorating sugar on top. Let icing set at room temperature before serving.