Combine 1 cup heavy cream, 1/2 cup sugar, and 1 tsp vanilla in a bowl. Whip on high speed for 3-4 minutes until soft peaks form—the mixture should double in volume and hold its shape briefly. This becomes your mascarpone base layer.

Fold the whipped cream gently into mascarpone with a spatula, turning the bowl as you fold. Use under-over motions to maintain airiness—this pumpkin tiramisu depends on texture contrast. The mascarpone layer should feel light and cloud-like, never dense or grainy.

In a separate bowl, whip the remaining 1 cup heavy cream with 1/4 cup sugar and 1 tsp vanilla for 3-4 minutes until stiff peaks form. Fold in pumpkin puree, pumpkin pie spice, and salt with CIA-level precision, folding just until the streaks disappear.

Combine cooled coffee and coffee liqueur substitute in a shallow dish. Working quickly, dip each ladyfinger into the coffee mixture for exactly 1 second per side—too long and they dissolve, too short and they stay dry. Arrange 12 dipped ladyfingers in a single layer across your 9x13 baking dish bottom.

Spread half the mascarpone mixture over the ladyfinger layer, smoothing gently. Then spread half the pumpkin cream over the mascarpone—the layers should be visible and distinct when finished.

Repeat steps 4 and 5: dip remaining 12 ladyfingers and arrange them over the pumpkin layer. Top with remaining mascarpone, then remaining pumpkin cream, spreading evenly to seal the layers.

Dust the top with cocoa powder and cinnamon using a fine sieve held 6 inches above the surface. Drizzle caramel sauce decoratively across the top in thin streams. Refrigerate for at least 30 minutes before serving—the creamy pumpkin tiramisu recipe needs this time for layers to set and flavors to meld.