Position an oven rack in the center and preheat to 350°F (175°C). Lightly spray a 9-inch tart pan with a removable bottom and place it on a rimmed baking sheet.
Pulse the chocolate wafer cookies in a food processor until fine and sandy. Measure 1 3/4 cups of crumbs into a medium mixing bowl.
Stir the sugar and 1/4 teaspoon salt into the crumbs, then pour in the melted butter and mix until the crumbs look like damp sand. Press firmly across the bottom and up the sides of the tart pan using the flat bottom of a measuring cup.
Bake the crust for 10 minutes, until it smells chocolatey and looks set. Remove from the oven and let it cool on the baking sheet while you make the filling; keep the oven at 350°F (175°C).
Whisk the pumpkin puree and sweetened condensed milk until smooth. Add the eggs, pumpkin pie spice, vanilla, and 1/2 teaspoon salt, whisking gently until combined without whipping in too much air.
Pour the filling into the slightly cooled crust to about 1/4 inch below the rim, and tap the baking sheet gently on the counter to release air bubbles. Bake for 45 to 55 minutes, until the edges are set and the center only jiggles slightly, reaching about 170°F (77°C). Tent the edges with foil if they darken too quickly.
Move the tart, still on its baking sheet, to a wire rack and cool at room temperature for 1 hour. Chill in the refrigerator for at least 1 more hour before adding the ganache.
Place the chopped dark chocolate in a heatproof bowl. Heat the cream until it steams and tiny bubbles form around the edge but does not boil hard, then pour it over the chocolate and let it sit for 2 minutes. Stir slowly until smooth and glossy, add the butter, and stir until melted. Let the ganache cool for about 10 minutes until slightly thickened but still pourable.
Pour the ganache into the center of the cold tart and spread it gently to the edges with an offset spatula. Tap the pan on the counter to level the surface, then refrigerate for 1 hour until the ganache is set.
Set the tart on top of a sturdy can or jar and let the outer ring slide down. Slide the tart onto a serving plate, sprinkle with flaky sea salt and chopped crystallized ginger if desired, and serve each slice with whipped cream.