3 cups (about 1 pound) pitted sweet cherries, quartered
1 cup granulated sugar, divided
1 1/2 cups whole milk
1 1/2 cups heavy cream
4 large egg yolks
2 teaspoons vanilla extract
3 ounces semisweet chocolate, finely chopped
2 teaspoons canola oil
In a small saucepan, stir together the cherries and 1/4 cup of the sugar. Simmer over medium heat about 8 minutes or until the sugar dissolves and the sauce thickens slightly. Let cool.
Set a medium sized bowl over a large container of ice water.
In a medium saucepan over medium heat, heat the milk, cream and 1/2 cup sugar stirring occasionally, until steam appears and the liquid is hot (175 degrees) about 5 minutes.
When the milk mixture is cooking, in a separate bowl, whisk the yolks and 1/4 cup of sugar together until smooth. Slowly whisk about 1 cup of the hot milk mixture into the yolks to temper them. Then slowly whisk the tempered yolk mixture back into the remaining hot milk mixture. Continue to cook the custard mixture over medium heat until it is very hot but not simmering (180-185 degrees). Immediately pour custard into bowl set in the ice bath and let cool, stirring occasionally, for about 10 minutes. Remove the custard mixture from the ice bath. Stir in vanilla extract. Cover tightly with plastic wrap and refrigerate until very cold (40 degrees), at least 4 hours and up to 24 hours.
A few minutes before you plan to churn the ice cream, place semisweet chocolate in a medium heatproof bowl. Set bowl over saucepan containing barely simmering water; heat mixture until chocolate is melted and whisk until smooth. Stir in oil and transfer to a ziploc bag; set aside.
Pour the mixture into the ice cream canister and churn following the manufacturer’s instructions until the mixture resembles the consistency of thick whipped cream. Add the cherry mixture. A Snip the corner of the ziploc bag that the chocolate is in, and while the machine is running, slowly drizzle the chocolate into the ice cream. After chocolate is added, continue churning until the mixture resembles soft served ice cream.
Transfer the ice cream to an airtight container. Cover the container and freeze the ice cream until it is firm, about 3 hours.