Step 1Place 2 of the coffee ice cubes in an Old-Fashioned glass. Add the cherry brandy, simple syrup and bitters.
Step 2With a potato peeler, peel 2 strips from the orange over the glass (so any oil from the orange skin falls into the glass). Twist the peels and drop them into the glass. Stir for 15 to 20 seconds.
Step 3Add 1 ounce rum and 2 coffee ice cubes and stir for 15 to 20 seconds. Add the remaining 1 ounce rum and 2 coffee ice cubes. Stir for 15 to 20 seconds to slightly melt the ice cubes. Add 2 to 4 coffee ice cubes to fill the glass.
Step 4Garnish with a Grand Marnier-soaked cherry, if using, and serve.