Make the Filling: In a small saucepan, combine cranberries, sugar, 1 tbsp orange juice, and water. Bring to a simmer over medium heat. Cook for 10-15 minutes until cranberries burst and the mixture thickens. Let cool completely.

Cream Butter and Sugar: In a large bowl, beat softened butter and sugar with an electric mixer until light and fluffy, about 2-3 minutes.

Combine Wet Ingredients: Beat in the egg yolk, vanilla extract, and orange zest until just combined.

Add Dry Ingredients: In a separate bowl, whisk together flour and salt. Gradually add the dry mixture to the wet ingredients, mixing on low speed until a soft dough forms.

Chill the Dough: Form the dough into a disk, wrap in plastic, and refrigerate for at least 1 hour.

Preheat and Prepare: Preheat oven to 375°F (190°C). Line a baking sheet with parchment paper.

Shape Cookies: Roll chilled dough into 1-inch balls. Place them 2 inches apart on the baking sheet. Use your thumb or the back of a 1/2 tsp measuring spoon to make an indentation in the center of each ball.

Fill and Bake: Spoon about 1/2 teaspoon of the cooled cranberry filling into each indentation. Bake for 12-15 minutes, until the edges are lightly golden.

Cool: Let cookies cool on the baking sheet for 5 minutes before transferring to a wire rack to cool completely.

Glaze: Once cool, whisk powdered sugar and 1-2 tsp orange juice to make the glaze. Drizzle over the cookies. Let the glaze set before storing.