Preheat oven to 400°F (200°C).

In a 10-inch ovenproof skillet, whisk together brown sugar, 2 tablespoons (30 grams) bourbon, and honey. Stir in pineapple.

Bake, stirring every 10 minutes, until pineapple is golden brown and liquid is thick and syrupy, about 30 minutes. Let cool for 5 minutes.

Transfer mixture to the container of a blender, and add 2 tablespoons (30 grams) bourbon and vanilla; blend until smooth.

In a large bowl, whisk together pineapple mixture, confectioners’ sugar, salt, and remaining 2 tablespoons (30 grams) bourbon. Use immediately, or cover and refrigerate for up to 3 days. If refrigerating, reheat glaze in the top of a double boiler before using.