To mix, stir pomegranate molasses and sugar at the bottom of a cocktail shaker until well combined. Stir in lime juice and add ice to fill the shaker.
Add gin, Bénédictine, Cherry Heering, and pineapple-orange juice. Shake vigorously for one minute. Add a dash of bitters and gently shake a few times to roughly combine.
Strain into tall glasses with lime wedge to garnish. Cut with club soda to serve a crowd.
For a punch variation of this cocktail, use the same ingredients but change the quantities to 5 parts gin, 4 parts Bénédictine, and 4 parts Cherry Heering. Stir together pomegranate molasses and sugar at the bottom of a pitcher. Add lime, gin, Bénédictine, Cherry Heering, and pineapple-orange juice. Stir until well combined, add a dash of bitters to taste. Serve over ice, topped off with club soda. Enjoy!