For the Maple Panna Cotta: Pour 1/2 cup (125 ml) of the milk into a large bowl. Sprinkle the gelatin over the milk and let rest about 5 minutes (don’t mix—this step allows the gelatin to bloom).
Pour the rest of the milk (1/2 cup / 125 ml) and the heavy cream in a saucepan. Whisk in the maple syrup and vanilla extract. Heat over medium heat until you reach a light simmer.
Pour the very hot milk mixture over the gelatin and whisk until the gelatin is completely dissolved. Divide the maple panna cotta mixture between 8 small glasses, bowls, or ramekins. Cover with plastic wrap and refrigerate at least 4 hours to set.
For the Pecan-Maple Crumble: Preheat the oven to 350°F (175°C). Line a baking sheet with parchment paper. In a large bowl, mix the flour, maple sugar, and chopped pecans together. Add the cold butter and incorporate it to the dry ingredients using a pastry cutter, a fork, or your hands, until the mixture forms pea-sized crumbs. Spread the mixture on the cookie sheet and bake for 10 minutes until the crumbs are golden (mixing the crumbs two to three times during baking allows them to brown more evenly). Let cool completely. Store the crumble in an airtight container at room temperature until ready to use. (The crumble will keep for up to three days.)
Prepare the Cara Cara orange layer: In a small bowl, combine the diced Cara Cara oranges and maple syrup. Spoon some of the oranges over each panna cotta.
SERVING: Right before serving, top each Maple Panna Cotta with a generous sprinkle of crumble.
MAKE-AHEAD TIP: The Maple Panna Cotta can be prepared up to two days ahead. Garnish with Cara Cara oranges and pecan-maple crumble right before serving.
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