In a bowl, combine the cookie crumbs with the butter and salt.

Mix with your fingers or a fork until all the crumbs are moistened.

Set aside 2 tablespoons for later in an airtight container.

Press the remaining mixture into the bottom of 8 small 8-ounce mason jars. Set jars aside.

In a heavy-bottomed saucepan, combine the sugar and water.

Cook over medium heat, stirring gently until the sugar dissolves.

Stop stirring and increase the heat to medium-high.

Cook until a candy thermometer temps between 210 and 220 F.

Remove from heat.

In a small bowl, whisk the remaining 1/2 cup of milk and cornstarch.

Heat 2 1/2 cups milk in a small saucepan to a gentle simmer; Set aside.

Whisk the egg yolks quickly in a large bowl.

Carefully pour in the hot milk and then the cornstarch, whisking constantly.

Lastly, whisk in the caramel until smooth.

Pour the mixture back into the heavy-bottomed saucepan and cook, stirring constantly, over medium heat to 175 F and the pudding thickens (3 to 7 minutes about).

Remove from heat and stir in the butter, one tablespoon at a time.

Whisk in the rum, and salt.

Strain the mixture if needed using a fine mesh sieve.

Divide among prepared mason jars with the cookie crumble.

Cover with plastic wrap pressing directly onto the surface of each pudding and chill until set, at least 4 hours.

Split the vanilla bean down the center and scrape the seeds out carefully.

Add the bean to the measuring cup of heavy cream and allow to sit for a few minutes.

Meanwhile, stir the sugar, corn syrup, and water in a clean heavy bottom saucepan and allow the sugar to dissolve over medium heat, stirring gently.

Stop stirring and increase the heat to a boil over medium-high.

Allow the sugar to cook for 5 to 8 minutes, for a rich deep amber color, watching closely as to not burn the sugar).

Remove from heat and carefully stir in the vanilla cream. It will bubbly up, just keep whisking rapidly.

Return to medium heat and whisk until creamy, about 2 to 4 minutes.

Remove from heat and stir in the butter and salt until nice and smooth.

Allow to cool before transferring to an airtight container.

Beat the cream in the bowl of your stand mixer over medium speed for 30 seconds.

Add the vanilla and sugar and increase the speed to medium-high.

Whip to soft, moist peaks, 3 to 5 minutes.

Spoon the caramel sauce over each of the prepared chilled puddings.

Top with a dollop of whipped cream and sprinkle the reserved cookie crumbles.