Chop or pulse dried cranberries to break into smaller pieces.
Whisk flour and sugar.
Cut butter into small pieces. Use a pastry cutter/fork/food processor to blend into small crumbs with flour mixture.
Stir in dried cranberries, salt, vanilla extract, almond extract, orange zest, and orange juice.
Mix until a large dough ball forms. I used a food processor but a stand mixer with a paddle attachment works, too or simply form the dough with your hands.
Wrap in plastic wrap and chill at least 2 hours or overnight.
Preheat oven to 325°F. Line a baking sheet with parchment paper.
Scoop ¾ cookie dough and roll into a smooth ball. Place dough 1½ inches apart.
Press thumb into center of dough ball.
Bake in oven for 14-16 minutes.
Press thumbprint or ½ tsp into center of baked dough again.
Melt chocolate in a double boiler on low heat with cream or in a microwave on power level 4 until melted. TIP: Avoid using a spatula to stir mixture as the moisture from it can seize it. Use a metal spoon to stir.
Fill the center of each cookie with white chocolate.
Drizzle the tops of the cookies with white chocolate using 2 spoons dipped in the chocolate or simply whisk together powdered sugar and water until smooth then drizzle over the top of each cookie.