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Add the bourbon, strawberry-vanilla syrup and Angostura bitters to a double rocks glass filled with 1 large ice cube and stir for 18 to 20 seconds, then add a few more ice cubes.
Express the oil of an orange peel, then drop the peel in the glass.
Add 1 cup water, 1 cup granulated sugar and the seeds scraped from 1 vanilla bean to a saucepan.
Bring to a low simmer until the sugar dissolves, then add 2 cups sliced strawberries and simmer on low for 15 minutes.
Remove from the heat, mash the strawberries and let cool.
Strain out the solids.
Store the syrup in the refrigerator for up to 1 week.