Line 2 baking sheets with wax paper. Lightly butter the wax paper or spritz lightly with cooking spray. Set aside.
Place the unwrapped caramels into a heavy bottomed saucepan with 1/4 cup heavy cream. Over medium-low heat, melt together stirring periodically, until the caramels have melted and is completely smooth.
Remove from the heat and add the vanilla. Mix thoroughly.
Return to the stove top, on the same burner with the heat turned off. Add the cashews and stir until completely coated.
Spritz a Tbsp or a small ice cream scoop with cooking spray and begin to separate the mixture into clusters, placing onto the wax paper lined baking sheet. Work quickly.
Allow the clusters to sit until firm.
After the clusters have set-up, melt the chocolate chips together with the vegetable shortening in a double boiler until completely smooth.
Drizzle over the clusters then sprinkle the tops with sea salt. Store in an airtight container at room temperature or chilled for up to 2 weeks. (If chilled, bring to room temperature prior to serving.)