Place a rocks glass (or coupe if preferred) in the freezer or fill it with ice water to chill while you prepare the cocktail. Fill a mixing glass or large Boston glass with ice to chill it as well.

Measure and add ingredients

Into the chilled mixing glass, pour 2 oz Jack Daniel's, 1 oz sweet vermouth, and 1/4 oz Benedictine. Add 2 dashes Angostura bitters and 1 dash orange bitters.

Stir

Using a bar spoon, stir the mixture briskly but smoothly for about 20–30 seconds (roughly 20–30 full spoon rotations) until the outside of the mixing glass becomes well chilled and slightly frosted. Aim to dilute the cocktail by about 20–25% — the temperature and slight dilution are important to balance the spirit and sweet vermouth.

Prepare serving glass

Discard the ice water from the chilled rocks glass (if used) and add one or two large ice cubes or a single large sphere. Alternatively, serve neat in a chilled coupe without ice if preferred.

Strain and garnish

Double-strain the stirred cocktail into the prepared glass using a hawthorne or julep strainer. Thread the Luxardo cherry on a cocktail pick and place it on top or drop it into the glass. Express the oils of the orange peel over the drink by holding the peel skin-side down about 3–4 inches above the surface and giving it a firm squeeze; then rub the peel around the rim and drop it into the glass (or use as a twist garnish).

Serve

Serve immediately. Recommend tasting and adjusting future pours if you prefer a slightly sweeter drink (increase vermouth by 1/4 oz) or a drier, more spirit-forward profile (reduce vermouth by 1/4 oz).

Optional / Notes

If you don't have Benedictine, a small dash (1/8–1/4 oz) of another herbal liqueur (e.g., amaro or yellow chartreuse) can be used, but flavor will vary. For a brighter citrus note, add an additional dash of orange bitters.