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Heat oven to 350 F. Line a rimmed baking sheet pan with parchment paper.
Place pitted prunes in a heatproof bowl. Pour boiling water over to cover. Let soak 15 minutes. Drain and briefly dry on a paper towel.
Wrap each soaked and dried prune with a half-slice of bacon. Place on parchment-lined baking sheet pan and bake 5 minutes.
Turn each piece over and continue to bake until bacon is crispy about 10 more minutes.
Remove from oven and drain on paper towels. Pierce each piece with a frilled toothpick, if desired, and serve while still warm. Be careful. The prune interior gets very hot!