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Preheat oven to 375°F. Line a baking sheet with parchment paper or a silicone baking mat. Set aside.
In a medium bowl, whisk together flour, baking powder and salt. Set aside.
In a stand mixer, beat together the butter and sugar until light and fluffy. Add cranberry jelly, egg and vanilla extract, mixing until combined.
Add flour mixture ½ cup at a time, mixing until completely combined.
Using a medium cookie scoop, drop one tablespoon of rounded dough onto prepared pan. Lightly flatten into a disk shape with the bottom of a buttered and sugared glass.
Bake for 10 minutes. The cookies will not look browned or cooked, but they are! Remove from oven and let cookies rest on baking sheet for 5 minutes. Then transfer to a wire rack to cool completely.
In a small bowl, toss together cranberries and sugar, set aside. In a small bowl, whisk together powdered sugar, milk and vanilla extract - until smooth.
Using a spoon, smooth icing onto the top of each cookie. Sprinkle with sugared craisins and let set for 10 minutes, or until hardened. Enjoy!