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Prepare 5 shot glasses. Add one stemless maraschino cherry to the bottom of each. Distribute the grenadine evenly among the 5 shot glasses.
Add the pineapple juice and cake vodka to a cocktail shaker with ice. Shake to combine.
Place the back of a bar spoon right above the cherry layer and slowly strain the vodka mixture over it to keep the layers separated.
Serve immediately.
Calories: 80kcal (4%)