Pumpa Tiramisu

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1. 1
   Whisk 3 Tbsp. bourbon, 3 Tbsp. (38 g) dark brown sugar, 1 Tbsp. plus 1 tsp. instant espresso powder, a pinch of kosher salt, and 1½ cups hot water in a wide shallow bowl until sugar and espresso are dissolved. Set bourbon mixture aside.
2. 2
   Pour water into a medium saucepan to come 2" up sides and bring to a simmer. Whisk 3 large egg yolks, 1 Tbsp. vanilla extract, and remaining ½ cup (packed; 100 g) dark brown sugar in a medium heatproof bowl. Set bowl over saucepan (do not let it touch the water) and reduce heat to low. Cook, whisking vigorously, until pale yellow and tripled in volume, about 5 minutes. Remove bowl from heat; add one 15-oz. can pumpkin purée and whisk to combine. Set pumpkin mixture aside.
3. 3
   Using an electric mixer on medium-high speed, beat, 1½ cups chilled heavy cream, ¾ cup mascarpone, and 1 tsp. Diamond Crystal or ½ tsp. Morton kosher salt in a medium bowl until stiff peaks form, 1–2 minutes. Add reserved pumpkin mixture and beat until no streaks remain.
4. 4
   Working one at a time, dip 10 crisp ladyfingers into reserved bourbon mixture, submerging just until saturated but not falling apart, about 5 seconds per side. Arrange ladyfingers in an even layer in a 3-qt. oval or 8x8" baking dish. Scrape in half of mascarpone whip and spread evenly to cover cookies. Repeat dipping process with remaining 10 crisp ladyfingers and arrange in baking dish over mascarpone whip. Scrape in remaining mascarpone whip and spread evenly over cookies, creating decorative swooshes and swirls as desired. Chill tiramisu at least 4 hours.
5. 5
   Just before serving, mix 1½ tsp. Dutch-process cocoa powder and 1½ tsp. ground cinnamon in a small bowl to combine. Dust over tiramisu with a fine-mesh sieve. Do Ahead: Tiramisu (without cocoa-cinnamon dusting) can be made 3 days ahead. Cover and keep chilled.