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Preheat oven to 375 degrees F.
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Wash, clean and pat dry the strawberries and remove tops. Cut the strawberries into quarters or in half, based on their size.
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In a medium bowl, whisk together honey, balsamic vinegar, sugar, and vanilla. Add the strawberries and toss to combine.
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Cover a rimmed baking sheet with parchment paper, and roast for 12-15 minutes, until strawberries are just tender.
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Remove from the oven and transfer the mixture to a bowl to cool slightly, it will thicken as it cools.
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Place Brie in a clean baking dish lined with parchment and bake for 10-15 minutes, or until cheese is soft and warm, but not melting out of the rind.
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Remove from the oven, top with the strawberry syrup and serve with crackers.