Prepare the Beijinho: In a nonstick saucepan, combine the sweetened condensed milk, coconut flakes, and butter. Cook over medium-low heat, stirring constantly for 5–7 minutes, until the mixture thickens and pulls away from the sides of the pan, resembling a soft fudge. Pour onto a plate, cover tightly with plastic wrap pressed directly onto the surface, and let cool completely.
Make the prune jam: In a small saucepan, combine the CA Prunes, orange peel, orange juice, and red wine. Bring to a gentle simmer and cook uncovered for about 15 minutes, or until the prunes are soft and the liquid has reduced to a thick, glossy syrup. Let cool.
Tip: Ideally, prepare both the beijinho base and the stewed prunes jam one day ahead so they have ample time to cool.
Roll the Beijinhos: Once the beijinho fudge is completely cool, use a half-tablespoon measuring spoon to portion the mixture onto a plate; you should get about 20–22 pieces. Lightly butter your hands to prevent sticking. Pick up each portion and gently roll it between your palms to form smooth, round balls about 1 inch (2.5 cm) in diameter.
Roll each ball in unsweetened coconut flakes (preferably fine shred) until fully coated. Place the finished beijinhos on a plate or parchment-lined tray. Refrigerate until ready to swirl into the ice cream base.
Make the ice cream base: In a small bowl, whisk together the dulce de leche, vanilla extract, and 1 cup of heavy cream until smooth and slightly airy. Set aside.
In a large bowl, whip the remaining 2 cups of heavy cream with a hand mixer or whisk until soft peaks form. (I recommend avoiding a stand mixer here to prevent overwhipping.)
Gently fold the dulce de leche mixture into the whipped cream, whisking carefully to incorporate some loft but avoiding overwhipping.
Swirl and freeze: In a freezer-safe container (preferably with a lid), pour half the ice cream base. Dollop spoonfuls of the prune jam and gently swirl with a spoon or butter knife, taking care to maintain distinct ribbons. Scatter about half of the beijinho balls evenly over the layer.
Pour the remaining ice cream on top, then repeat the prune dollops, swirl, and sprinkle with the remaining beijinhos. You may have a couple of beijinhos left over—save these to serve alongside the ice cream.
Freeze for at least 6 hours, preferably overnight.
To serve, scoop generously and finish with a pinch of flaky sea salt. Each bite should be packed with creamy, caramelized sweetness, rich and tart prune jam, and an unmistakable chew of coconut.