Pineapple Cake Old Fashioned Recipe

Make pineapple cake–infused simple syrup

Combine 1 cup granulated sugar and 1 cup water in a small saucepan over medium heat. Stir until sugar dissolves and the mixture just begins to simmer. Remove from heat, add 3 oz crumbled pineapple cake pieces, and let steep, covered, for 20–30 minutes off heat, stirring once or twice to help dissolve cake crumbs into the syrup.

After steeping, press the solids through a fine mesh strainer or cheesecloth into a clean container, extracting as much liquid as possible. Discard solids. Stir in 1/4 tsp vanilla extract and a pinch of kosher salt. Cool to room temperature; refrigerate. Yield: about 1 1/4 cups flavored simple syrup. Use 3/4 oz per cocktail (recipe calls for 0.75 oz).

Make toasted pineapple reduction (garnish syrup)

Heat a skillet over medium-high and add 1 tbsp unsalted butter. When foam subsides, add 2 tbs light brown sugar and 4 slices fresh pineapple. Cook, turning occasionally, until pineapple is caramelized and toasted on both sides, about 2–3 minutes per side. Remove pineapple slices; reserve one for garnish and chop remaining pieces fine. Add chopped caramelized pineapple back to skillet with any juices and simmer 1–2 minutes to concentrate. Remove from heat and let cool slightly. Transfer to a small bowl and press through a fine mesh strainer to collect a thick toasted pineapple reduction, about 1–2 oz. Stir into the infusion syrup (or keep separate and use 1/4 oz per cocktail to float).

Cool all syrups to room temperature. Refrigerate if not using immediately. Syrups will keep up to 7 days refrigerated.

Place a large ice cube in an old fashioned glass.

Add 2 oz bourbon, 0.75 oz pineapple cake–infused simple syrup, 0.25 oz toasted pineapple reduction (or a 1/4 oz float), and 2 dashes Angostura bitters into a mixing glass with ice. If you prefer a slightly sweeter drink, increase infused syrup to 1 oz.

Stir the mixture with a bar spoon for 20–30 seconds until well chilled and slightly diluted (aim for about 15–20% dilution).

Strain the cocktail over the large ice cube in the old fashioned glass. If you have reserved a small amount of toasted pineapple reduction, spoon it gently on top for a glossy floated layer.

Express the oils of the orange peel over the drink by holding it skin-side down and giving it a quick twist, then rub the peel on the glass rim and drop it in.

Garnish with the toasted pineapple slice on the rim or skewered and serve immediately.