Muddle the Mandarin: In a shaker, muddle the mandarin segments to release their juice and essential oils. You want to break them down well to blend the flavors into the drink.

Add Liquids: Pour the Bourbon, Grand Marnier, sweet Vermouth, and a few dashes of Angostura bitters into the shaker.

Shake: Fill the shaker with ice, covering the liquid. Secure the lid and shake vigorously for about 15 seconds to chill and mix the ingredients thoroughly.

Strain and Serve: Strain the mixture into a rocks glass filled with fresh ice. The straining helps remove the mandarin pulp, leaving you with a clear, smooth cocktail.

Garnish: Optionally, garnish with a sprig of mint or a wheel of mandarin on the rim of the glass for an extra touch of flair.

Enjoy: Serve immediately and enjoy the vibrant, citrusy notes of your Orange Bourbon Smash.