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Step 1
Preheat oven to 400°. In an 8-in. cast-iron or other ovenproof skillet, melt butter over medium heat; stir in brown sugar and vanilla until dissolved. Arrange orange slices in a single layer over brown sugar.
Step 2
On a lightly floured surface, unfold puff pastry. Roll to a 9-in. square; place over oranges, tucking in corners.
Step 3
Bake until tart is golden brown and filling is heated through, 20-25 minutes. Cool for 10 minutes before inverting onto a serving plate. Serve warm, with ice cream if desired.