For the Apple Pie Filling:
Preheat the oven to 375 degrees F.
In a large bowl, combine brown sugar, vanilla, cinnamon, nutmeg, cloves, and salt. Mix together. Toss in the apples and coat them with the mixture. Transfer apples into an 8×8 baking dish.
Bake for 30 minutes, or until tender and juicy. Remove from the oven, transfer into a heatproof bowl, and allow to come to room temperature.
For the Caramel Swirl:
While the apples bake, start on the sauce. Coat the bottom of a saucepan with granulated sugar.
Set heat to medium-low. As the sugar dissolves and melts into a clear liquid, swirl it around to ensure all sugar melts.
Once melted and golden, add heavy cream and whisk quickly. It will bubble furiously. Continue whisking until the caramel thickens to a rich and smooth sauce.
Once smooth, turn off the heat, stir in salt and vanilla, and let cool to room temperature.
For the Crust Crumbles:
Preheat the oven to 400 degrees F and line a baking sheet with parchment paper. Break the pie crust into varying sizes and arrange on the baking sheet.
Bake for 13-15 minutes, or until golden-brown and crisp. Cool completely, then crush into crumbs, leaving some larger chunks.
For the Ice Cream:
In a mixer, beat cream cheese on medium-high speed, then slowly add condensed milk and vanilla extract until smooth.
Fold whipped cream into the cream cheese mixture using a spatula.
To Assemble:
Fold ¾ of the apples into the batter, folding just 3-4 times until apples are swirled through. Drizzle on cooled caramel sauce.
Repeat with ¾ of the crust crumbles, folding 3-4 times.
Transfer to a large airtight, freezer-safe container. Top with remaining apples and crumbles, and drizzle with more caramel sauce.