To prepare phyllo, line a large baking sheet with parchment paper; coat paper with cooking spray.
Place 1 phyllo sheet on paper (cover remaining dough to keep from drying); lightly brush with 1/2 teaspoon oil.
Sprinkle with 1 teaspoon powdered sugar. Repeat layers five more times with remaining 5 phyllo sheets, remaining 2 1/2 teaspoons oil, and remaining 5 teaspoons powdered sugar.
Cut phyllo stack lengthwise into 3 equal strips; make 5 crosswise cuts to form 18 pieces.
Coat another sheet of parchment paper with cooking spray; cover phyllo stack with paper, coated side down.
Place another baking sheet on top of phyllo stack to weigh it down.
Bake at 350 for 15 minutes or until golden brown and crisp. Carefully remove top baking sheet and top piece of parchment. Cool phyllo pieces on a wire rack.
To prepare figs, combine port, figs, and cinnamon stick in a saucepan over medium-high heat; bring to a boil.
Remove from heat; cover and let stand 10 minutes.
Remove figs with a slotted spoon; set aside. Discard cinnamon stick. Bring port to a boil over medium-high heat, and cook until reduced to about 2 tablespoons (about 2 minutes).
Remove from heat; stir in reserved figs, 1 tablespoon oil, and salt. Cool to room temperature.
To prepare cream, combine cream cheese, juice, and honey in a small bowl; beat with a mixer at low speed 30 seconds or until smooth. Cover and chill 30 minutes.
Place 1 phyllo piece on each of 6 dessert plates. Top each serving with about 2 teaspoons cream and about 1 tablespoon fig mixture. Repeat the layers once, and top each serving with 1 phyllo piece.
Sprinkle evenly with 1 tablespoon powdered sugar.
Serve immediately.
Wine note: You'll need some port to prepare this recipe, so make it a bottle you can enjoy right alongside this richly layered and wonderfully textured dessert. A tawny port, like Dow's 10 Years Tawny ($31), provides ample sweetness. And wood aging imparts tawnies with nutty, dried fruit, and treacle flavors that echo those found in the dessert. --Jeffery Lindenmuth
