In a medium bowl, place espresso; stir in 1½ tablespoons (18 grams) sugar until dissolved. Stir in wine.

In the bowl of a stand mixer fitted with the whisk attachment, beat cold cream and vanilla, starting at lowest speed and gradually increasing mixer speed to medium-high, until stiff peaks form, about 2 minutes. Transfer to a medium bowl; cover and refrigerate until ready to use.

Clean bowl of stand mixer and whisk attachment.

In the heatproof bowl of a stand mixer, whisk together egg yolks and remaining 1¼ cups (250 grams) sugar by hand. Place bowl over a saucepan of simmering water; do not let the bottom of the bowl touch the water. Cook, whisking frequently, until an instant-read thermometer registers at least 110°F (43°C). (See Note.)

Carefully return bowl to stand mixer. Using the whisk attachment, beat at medium-high speed until thick and ribbon-consistency, 2 to 3 minutes. (Mixture will still have texture from the sugar.) Let cool for 5 to 10 minutes.

In another medium bowl, place mascarpone, and work with a spatula until softened, smooth, and creamy. Fold mascarpone into egg yolk mixture in two additions just until combined. Fold in whipped cream in two additions just until combined.

Quickly dip half of Ladyfingers in espresso mixture. (Do not let it soak.) Place in bottom of a 13x9-inch baking dish in a single layer, with long sides of Ladyfingers going along long sides of pan. (Trim or cut Ladyfingers, if needed, to make sure bottom of pan is fully covered.) Spoon half of mascarpone mixture (about 4 cups or 630 grams) on top of dipped Ladyfingers, and spread into an even layer. Dip remaining Ladyfingers in espresso mixture, and place on top of mascarpone mixture in pan. Top with remaining mascarpone mixture, smoothing into an even layer. Cover and refrigerate for 24 hours for best flavor and texture.

Before serving, using a fine-mesh sieve, dust top with cocoa. Using a vegetable peeler, grate chocolate, and sprinkle on top of cocoa powder. Serve immediately.