Preheat oven to 400°F. Pit and de-stem cherries.
Transfer cherries to a lined baking sheet and combine with olive oil, cinnamon, maple syrup, and a small pinch of sea salt.
Bake for 10 - 15 minutes until jammy and soft. Let cool.
Combine eggs, egg yolks, white sugar, vanilla extract, kosher salt, and cornstarch in a medium bowl. Whisk until light, pale, and fluffy.
Heat heavy cream and whole milk in a sauce pot over medium-high heat until scalding and beginning to bubble.
Slowly pour hot cream into egg mixture, whisking constantly. Once half is poured, add the rest and stir to combine.
Pour mixture back into the sauce pot. Cook over medium high heat for 5-10 minutes until thickened. Allow custard to cook on the bottom of the pan slightly.
Stir to combine and pour thickened custard onto a clean baking sheet. Add your cherries and stir to combine.
Chill baking sheet of custard in fridge for 15-30 minutes or in the freezer for 5-10 minutes until cold. In the meantime, prepare ice cream machine.
Pour custard and cherries into ice cream machine and churn for 20 - 30 minutes until stretchy and thick.
Spoon into a reusable ice cream storage container and freeze for at least 30 minutes before serving. Top with macerated cherries.