Make the Dough

1. Prepare the Dough: In a large bowl, combine the flour, sugar, baking powder, and salt. Add the chilled butter and use a pastry cutter or your hands to blend the butter into the dry ingredients until the mixture resembles coarse crumbs.
2. Add Wet Ingredients: Beat the eggs, vanilla extract, orange juice, and orange zest together in a small bowl. Slowly add the wet mixture to the dry ingredients, stirring until a dough forms.
3. Chill the Dough: Divide the dough into two balls, wrap them in plastic wrap, and refrigerate for at least 30 minutes. This will make the dough easier to work with.

Prepare the Filling

1. Combine the Filling Ingredients: In a food processor, combine the figs, dates, almonds (if using), honey, cinnamon, cloves, orange zest, and rum (or orange juice). Pulse until the mixture is finely chopped and forms a thick paste.
2. Chill the Filling: Transfer the filling to a bowl and refrigerate for 15 minutes to firm up.

Assemble the Cookies

1. Roll Out the Dough: Preheat your oven to 350°F (175°C) and line a baking sheet with parchment paper. Roll out one of the dough balls on a lightly floured surface to about 1/8-inch thickness.
2. Cut into Strips: Using a sharp knife or a pizza cutter, slice the dough into strips, about 2 inches wide.
3. Fill the Dough: Place a teaspoon of the fig filling along the center of each dough strip. Fold the sides of the dough over the filling to create a sealed log shape. Pinch the edges to seal.
4. Shape the Cookies: Gently curve each filled dough log into a crescent or an “S” shape, placing them on the prepared baking sheet.
5. Bake: Bake for 15-20 minutes, or until the cookies are lightly golden on the edges.
6. Cool: Let the cookies cool on the baking sheet for 5 minutes before transferring to a wire rack to cool completely.

Glaze and Decorate

1. Prepare the Glaze: In a small bowl, whisk together the powdered sugar, milk, and vanilla extract until smooth. Drizzle the glaze over the cooled cookies.
2. Add Sprinkles: If desired, top the glaze with sprinkles or colored sugar for a festive touch.