Make the filling: Pulse figs, walnuts, raisins, honey, zest, cinnamon, cloves, and chocolate in a food processor until a sticky paste forms. Set aside.

Mix the dough: Whisk flour, sugar, baking powder, and salt. Beat in butter until crumbly, then egg, vanilla, and 2 tbsp milk, adding the last tbsp only if needed. Shape into a disc, wrap, and chill at least 1 hour.

Roll and fill: Roll dough to a 12x8-inch rectangle. Spread filling evenly, leaving a 1-inch border on long sides. Roll up tightly from a long edge, pinch to seal, wrap, and chill 30 minutes.

Slice and bake: Preheat oven to 350°F (175°C). Slice log into 3/4-inch rounds, place cut side up on a parchment-lined sheet. Bake 15 to 18 minutes until edges are just golden. Cool 5 minutes on the sheet, then transfer to a rack to cool completely.

Glaze: Whisk powdered sugar, 1 to 2 tbsp milk, and 1/4 tsp vanilla. Dip or drizzle cookies, then let set 20 minutes.