Preheat oven to 375 degrees F. Line a baking sheet with parchment. Place strawberries on pan, and sprinkle evenly with ¼ cup sugar. Roast for about 25 minutes, until the strawberries are soft and syrupy. Let cool slightly, then puree and set aside in the refrigerator until ready to use.
While the strawberries roast, make the ice cream base. Add pink peppercorns, half and half, whipping cream, the 1 cup minus 2 tablespoons sugar, and the strawberry preserves to a large saucepan over medium heat. Bring to just barely a simmer. Once you see a bubble hit the surface, remove from the heat. Pour into a lidded container and let sit overnight for texture and flavors to develop.
Strain ice cream base mixture to remove peppercorns. Freeze according to your ice cream maker's instructions until soft serve consistency. Once it has reached this point, gently stir in the roasted strawberry puree into the ice cream. Place in a lidded container and let harden in the freezer for at least an hour before serving.