Add 2 Tablespoons butter to an oven-safe skillet and melt butter in oven. Add vanilla extract to butter and stir to combine.
Place strawberries, cut-sides down, in skillet and sprinkle with brown sugar. Bake at 400°F for 10 minutes or until berries are soft. Remove pan from oven.
With a slotted spoon, remove berries from pan and set aside to let cool.
Add wine and vinegar to skillet and simmer over medium heat until reduced slightly.
Remove from heat and whisk in chilled butter.
To serve, spoon ice cream into dessert bowls, top with warm strawberries and drizzle with sauce.
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