Mix all dressing ingredients in a small saucepan and bring to a boil over medium-high heat
Reduce the heat to medium-low and simmer until thickened, 3 to 5 minutes.
Take the pan off the heat and set aside.
Preheat the oven to 450°F.
Place a chunk of pineapple and a slice of water chestnut in the center of a half-slice of bacon and wrap the bacon around then poke the toothpick through spearing the bacon, pineapple and chestnut and place it on a rimmed baking sheet. Assemble the rest of them the same way.
Bake in the preheated oven until bacon is crispy, 20 to 30 minutes.
Drizzle the rumaki with the sesame dressing and serve.
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