Add 2 oz rye whiskey, 1 oz sweet vermouth, 0.25 oz amaro, 2 dashes Angostura bitters, 1 dash orange bitters, and 0.25 tsp simple syrup (optional) into the mixing glass.

Add ice and stir

Fill the mixing glass with large ice cubes (enough to come just above the liquid). Using a bar spoon, stir gently but thoroughly for 25–30 seconds until the mixture is well chilled and properly diluted (glass will feel cold and slightly frosted).

Strain

Discard ice from the chilled serving glass (if used). Using a Hawthorne or julep strainer, strain the stirred cocktail into the chilled rocks or coupe glass over a single large ice cube if serving on the rocks, or neat if using a chilled coupe.

Garnish & Finish

Express orange oil

Hold the orange peel with the exterior facing down over the cocktail. Firmly pinch and fold the peel to release the oils, expressing them over the surface of the cocktail. Optionally run the peel around the glass rim for extra aroma, then drop it into the drink or discard per preference.

Add cherry

Gently place one Luxardo or brandied cherry into the cocktail as the finishing garnish.

Serving

Serve immediately. Sip slowly to appreciate the layered sweetness of vermouth, the bitter herbal note of the amaro, and the backbone of the rye. If you prefer a slightly sweeter profile, add the optional simple syrup in the measuring step.