Mix dried cherries with brandy and let sit for at least 30 minutes and up to 2 hours.

Warm whole milk, heavy cream, granulated sugar, and brown sugar in the saucier over medium heat. Add split vanilla bean and continue stirring until the mixture is steaming but not boiling (about 160-170°F).

Whisk together eggs, egg yolks, salt, and vanilla extract – if using – in a large bowl. Slowly add the warmed milk, while whisking, to temper the eggs. Return 2 cups of the mixture to the saucier and cook over medium-low heat, constantly stirring, until the mixture is thick enough to coat the back of the spoon. Immediately remove from heat and stir in the 2–3 tablespoons of reserved brandy from the cherries. Transfer to a bowl and press parchment paper down against the liquid to keep it from forming a film.

(If you overcooked the custard and you find it’s lumpy, filter it through a fine mesh sieve to remove the solids and whisk in a few more tablespoons of heavy cream to smooth it out.)

Add cubed brioche, cherries, brandy-soaked dried cherries, and chocolate chips to the remaining un-cooked custard. Stir to combine, then transfer back to the saucier. Let sit for 20-30 minutes, while you preheat the oven to 350°F.

Cover the bread pudding and bake for 30 minutes. Uncover and bake for another 30-35 minutes, until the bread pudding is puffed and browned and cooked through.

Remove from the oven and serve immediately, drizzling on reserved brandy custard and topping with maraschino cherries, if desired.