Gather all ingredients.

Remove 20 of the cookies from 1 of the packages of chocolate cookies; set aside. Working in 2 batches, process remaining cookies (about 30 oz.) in a food processor until crushed into very fine crumbs, about 30 seconds. Transfer crumbs to a large bowl and add salt. Microwave 1 cup of the butter in a heatproof bowl on HIGH until melted, 30 to 60 seconds. Add melted butter to crumb mixture and stir until well combined.

Transfer crumb mixture to 2 ungreased deep dish (9- to 9 ½-inch) pie plates (about 3 cups per plate); firmly press crumbs into bottom and up sides of pie plates. Freeze crusts, uncovered, until firm, about 20 minutes.

Meanwhile, melt remaining ¼ cup butter in a large skillet over medium. Add pecans; cook, stirring often, until fragrant, 1 to 2 minutes. Stir in coconut; cook, stirring constantly, until toasted and golden, about 4 minutes. Transfer to a large baking sheet; spread in an even layer. Let cool completely to room temperature, about 20 minutes.

Beat together sweetened condensed milk, cream cheese, and vanilla in a large bowl with an electric mixer on high speed until smooth, about 1 minute. Stir in ½ container of the whipped topping to lighten the cream cheese mixture. Gently fold in remaining 1 ½ containers whipped topping in 3 batches until just combined.

Spoon about 2 cups of the cream cheese mixture into each cooled pie crust; spread into an even layer with an offset spatula. Drizzle about ⅓ cup of the caramel sauce on each cream cheese mixture in crusts; gently swirl into cream cheese mixture. Sprinkle 1 cup of the cooled coconut mixture on top of each pie. Coarsely crumble 5 of the reserved cookies onto each pie in an even layer. Repeat layers once more with remaining 4 cups cream cheese mixture, ⅔ cup of the caramel sauce, remaining 2 cups cooled coconut mixture, and remaining 10 cookies. Drizzle with remaining about ⅓ cup caramel sauce evenly over top both pies.

Cover with plastic wrap and freeze until firm, at least 4 hours or up to 24 hours. When ready to serve, remove pie from freezer and allow to stand at room temperature for 10 minutes before slicing.