Set a shelf in the lower third of the oven and preheat the oven to 375 degrees . Melt 1 1/2 tablespoons of the butter and use it to brush the inside of 4 ovenproof mugs. Dust the inside of the mugs with 1 tablespoon of the confectioners sugar and shake out the excess. Place the prepared mugs on a baking sheet and set aside.
Place the chocolate in a small microwave-safe bowl and microwave at medium power for 2 minutes. Stir, heat for 1 more minute, then stir until smooth.
Melt the remaining tablespoon of butter in a small saucepan over medium heat. Add the flour and stir to make a paste. Whisk in the milk and coffee and cook, whisking, until thickened, 2 to 3 minutes. Be sure to get into the corners of the pan. Remove from the heat; whisk in the melted chocolate and the vanilla, then the egg yolks.
In a grease-free medium or large bowl, beat the egg whites and cream of tartar at medium speed until soft peaks form. Gradually beat in the granulated sugar and then beat at high speed until stiff peaks form, 1 to 2 minutes. With a rubber spatula, fold one-third of the whites into the chocolate mixture, and then fold that into the remaining whites. Scrape the batter into the prepared mugs. (Depending on the size of your mugs, you may have enough souffle mixture for 1 or 2 extra servings.) At this point, you can cover and chill the souffles until ready to bake.
Place the caramels, 3 tablespoons of the cream and the salt in a small bowl; microwave at medium power for 2 1/2 minutes, until the caramels are melted and the sauce is smooth.
Bake the souffles until puffy and slightly cracked, about 15 minutes.
While the souffles bake, whip the remaining 3/4 cup of cream with the remaining 1 tablespoon of confectioners sugar until the whipped cream is stiff enough to hold its shape.
Place the hot mugs on small plates. Serve the souffles topped with the whipped cream and caramel sauce. Dust with cinnamon.