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Process raspberries and strawberries in batches in a food processor or blender until smooth. Transfer to a food mill or push through a fine sieve into a large measuring cup or bowl. Add enough water to the strained berries to equal 5 cups liquid.
Whisk cornstarch and water in a small bowl. Whisk the cornstarch mixture and granulated sugar into the strained berries and transfer to a Dutch oven or large saucepan. Cook over medium heat, whisking constantly (make sure to whisk the bottom well), until the mixture is very hot and beginning to bubble. Cook for 1 minute more, whisking constantly.
Transfer the pudding to a large bowl and let cool for 10 minutes. Press a piece of plastic wrap directly onto the surface and chill in the refrigerator for at least 2 hours (it will continue to thicken as it chills).
Whip cream in a small bowl until soft peaks form. Add confectioners’ sugar and vanilla; continue whipping until firm peaks form. Fold in yogurt. Serve the pudding with a dollop of cream on top.