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1
To make the pudding filling: In a heatproof bowl, whisk the cornstarch, sugar, salt, and cinnamon together. Slowly whisk in the milk until completely combined. Set the bowl over a saucepan of simmering water. Cook, whisking frequently, until the mixture thickens, about 15 minutes. Add the chopped chocolate and whisk to melt and combine. Continue cooking until the pudding is very thick and smooth. Remove the bowl from the pan and stir in the vanilla extract. Press a piece of plastic wrap against the surface of the pudding and chill for at least 30 minutes.
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2
To make the cupcakes: Preheat oven to 350 F. Line a cupcake pan with paper liners.
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3
Sift the flour, cornstarch, cinnamon, baking powder, baking soda, and salt into a medium bowl. In a 2-cup measuring cup combine the milk and vinegar and whisk to combine. Add the sugar, oil and vanilla, mixing until incorporated. Pour the wet ingredients over the dry ingredients and whisk until just combined. Divide the batter evenly among the prepared liners - about 2/3 full.
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4
Bake for about 18 minutes. Remove the pan to a wire rack and let the cupcakes cool for a few minutes before removing them to the rack to cool completely.
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5
To make the frosting: In a medium bowl, whisk the confectioners' sugar, cocoa powder, milk, meringue powder, cream of tartar and cinnamon until smooth. Refrigerate for at least 30 minutes - the mixture will firm up. Using a hand mixer, gradually beat the heavy cream into the chocolate mixture until completely incorporated. Continue beating until the frosting is fluffy, and reaches medium peaks. Chill until ready to use.
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6
To assemble the cupcakes: Use a small paring knife to cut a cone-shaped piece from the center of each cupcake. Fill the hole with the chocolate pudding, then replace the top portion of the cone. Transfer the chocolate whipped cream frosting to a pastry bag fitted with a tip. Pipe frosting into a swirl on each cupcake.
