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Place chopped chocolate in medium bowl. In small saucepan, combine ¼ cup heavy cream and Kahlua and heat on medium until simmering, 3 to 4 minutes (or microwave in bowl until hot, about 1 minute). Pour cream mixture over chocolate, let sit 5 minutes, then stir until smooth. Refrigerate until cool but still pourable, 10 to 15 minutes.
Meanwhile, in stand mixer fitted with whisk attachment on medium, beat mascarpone, confectioners’ sugar, espresso powder, vanilla, and a pinch of salt until smooth and creamy, 1 to 2 minutes.
Gradually add remaining 1¼ cups heavy cream and beat until stiff peaks form, 2 to 3 minutes.
Divide tiramisu dip among glasses, layering with chocolate sauce and gently folding to swirl. Dust with cocoa powder and serve with ladyfingers. Alternatively, in large bowl, fold chocolate sauce into dip and serve family-style.