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Combine sugar and vinegar in a small saucepan and bring to a simmer over medium heat until sugar is dissolved, 2-4 minutes
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Remove from heat, add cranberries, and set aside
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Combine Brussels sprouts, 2 tablespoons olive oil, 3/4 teaspoons of the salt, and red pepper flakes, toss to coat and transfer to a parchment paper lined baking sheet
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Broil in top 1/2 of oven for 6 minutes, stirring halfway through and rotating pan if necessary to get all browned
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Remove from oven, toss in bowl with the cranberry mixture, set aside
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Heat oven to 400
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Transfer bread slices to a baking sheet, use 1-2 tablespoons of the olive oil to brush all the bread slices
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Toast in oven for 5-6 minutes, until golden brown and toasty
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Stir together ricotta, 1/4 teaspoon, and remaining 2 tablespoons olive oil until well combined
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Spread each bread slice with ricotta, top with Brussels and cranberry mixture