Stir milk, pudding mix, and condensed milk together in a large bowl. Combine cream, sugar, and vanilla in another bowl and beat it until stiff peaks form. Save half of the cream mixture. Fold half of the cream and 1/3-cup of caramel into the pudding. Line a 3-quart dish with vanilla wafers. Spread a third of the pudding and bananas over the wafers. Drizzle caramel and sprinkle sea salt over the bananas. Repeat layers until the dish is full. Refrigerate the dessert for 3 hours. Garnish with the remaining cream and crumbled cookies.

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