Start by making the Calabrian chili brown sugar syrup. Add 1 cup water, 1 cup brown sugar, and 1 tablespoon chopped jarred Calabrian chilies. Heat on medium-low until all the brown sugar has melted, then let cool.
For the cocktail, add ice to a shaker then combine it with 2 ounces of reposado tequila, 1 ounce lemon juice, 1 ounce pineapple juice, and 1 ounce of the chili syrup. Shake for 30 seconds.
Pour into a tajin rimmed glass filled with ice and garnish with a chili pepper and dehydrated citrus.