In a small saucepan, add the cranberries and smash with a muddler or the bottom of a heavy glass. Add the sugar, water, rosemary, and honey and cook over medium heat for about 5 minutes, until all the sugar is dissolved and honey is fully incorporated. When cool, strain through a fine mesh sieve and pour into a storage container or squeeze bottle and refrigerate until ready to use.

Fill short rocks glass with ice. Muddle 8 cranberries in a cocktail shaker. Add bourbon, cranberry honey simple syrup, and ice. Shake until cold. Pour into rocks glass and garnish with a few fresh cranberries and a rosemary sprig.