In a microwave-safe bowl, bring the milk to a simmer in the microwave, about 1 minute. Add chopped chocolate, cover with plastic wrap, and allow to sit for 5 minutes. Stir until smooth; set aside.
In a medium mixing bowl, stir the sweetened condensed milk, cocoa powder, vanilla, and salt together until combined.
In the chilled bowl of a stand mixer fitted with a whisk attachment, whip the cream until stiff peaks form. Stir 1 cup of the whipped cream into the condensed milk mixture until combined and slightly lightened. Pour this mixture in with the rest of the whipped cream and fold together until no more white streaks remain. Place in freezer.
Coarsely chop the frozen chocolate-covered cherries.*
To assemble, pour 1/3 of the ice cream custard into an 8-inch square pan. Drizzle 1/3 of the chocolate sauce on top, swirl with a knife, then top with 1/3 of the chocolate-covered cherries. Repeat this process two more times until you've used up all of the ingredients. Cover with plastic wrap and freeze for at least 6 hours, or overnight.