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Hull and chop 2 cups fresh strawberries.
In a small saucepan, combine chopped strawberries, 2 tablespoons granulated sugar, and 1 tablespoon water. Cook over medium heat, stirring occasionally, for 5–7 minutes until thickened, then mash slightly and let cool completely.
Place 1 cup buttery shortbread cookies in a bag and crush into coarse crumbs. In a small bowl, melt 2 tablespoons unsalted butter and toss with the crumbs. Set aside.
In a large chilled bowl, pour in 2 cups cold heavy cream. Using an electric mixer, beat on medium-high speed until stiff peaks form (about 3–5 minutes).
Gently fold one 14-ounce can sweetened condensed milk into the whipped cream until just combined.
Spoon half of the ice cream base into a 9×5-inch loaf pan and spread evenly. Dollop half of the cooled strawberry swirl on top, then sprinkle half of the shortbread crumble.
Repeat with the remaining ice cream base, strawberry swirl, and crumble. Use a knife or skewer to gently swirl the layers, keeping distinct ribbons.
Cover the pan tightly and freeze for at least 6 hours (preferably overnight) until firm.
Before serving, let the ice cream sit at room temperature for a few minutes to soften slightly, then scoop into bowls or cones.