Your guests will do a double-take when they see this glossy cake that appears to have shards of glass floating in it! But no worries -- all those fragments are made from wine-infused gelatin. Trapped in a panna-cotta-like pudding with a shortbread crust, they make for a surprising and sweet finale to any meal.
Coat a 10-inch springform pan with cooking spray and set aside. Pulse the shortbread cookies in a food processor until finely ground, then add the butter and 2 tablespoons sugar and pulse until combined. Press the mixture into the bottom of the prepared pan and freeze until solid, about 1 hour.
Meanwhile, spray three 9-by-5-inch loaf pans with cooking spray and line with plastic wrap so that there is at least a 3-inch overhang on each side; spray the plastic wrap with cooking spray. Mix 2 packets gelatin into 1/2 cup cold water in a medium microwave-safe bowl until combined and let sit for 5 minutes to bloom; the mixture will get very stiff. Microwave on high power for 20 seconds, then stir to combine. Continue to heat and stir in 20-second intervals until the gelatin is completely dissolved, then stir in the red wine and 1/2 cup sugar until the gelatin is incorporated and the sugar is completely dissolved. Pour into one prepared pan. Repeat the process with the rose and white wines, respectively, then refrigerate all the pans until completely set, about 3 hours.
Meanwhile, mix the remaining 4 packets gelatin into 1 cup cold water in a large bowl; let stand 5 minutes. Add 1 cup boiling water and stir until dissolved; stir in the condensed milk until combined. Set aside to cool to room temperature, 2 to 3 hours. Skim the foam from the top.
Using the plastic wrap to help you, lift the wine jellies out of the pans and lay them on a clean baking sheet. Working one at a time, tear and break them up into irregular pieces about 1 inch wide and 2 to 3 inches long; they should look like broken shards of glass. Repeat with remaining wine jellies. Arrange all but 2 cups of the wine shards on the frozen shortbread crust. Pour the condensed milk gelatin slowly into the pan, avoiding pouring directly on the wine shards so that they remain brightly colored and don't develop a milky film. Arrange the remaining wine shards on top so that they are poking up slightly through the top of the milk gelatin. Chill until completely set, at least 3 hours (overnight is best). Open clasp to release the sides of the pan, then serve.
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