1/4 cup caramel ice cream topping, such as Smuckers
1 9" store-bought prepared graham cracker or sugar cookie crumb pie crust
Prepare the raisins at least one day ahead of when you're planning to serve the pie. Place the raisins, cinnamon, and rum in a clean glass jar or plastic container with lid. Keep it in the fridge and shake the container often, redistributing the rum so that all the raisins are able to plump up.
At least 4 hours before you're ready to serve the pie, take your vanilla ice cream out of the freezer, place it in a large bowl, and allow it to thaw until softened enough to work with, but not so soft it's runny.
When your ice cream is thawed, drain and discard (or save for future batches of rummy raisins!) the extra rum from the raisins, and add the raisins to the ice cream.
Blend thoroughly. You'll want to do this quickly so that the ice cream doesn't melt too much and make a mess when you spoon it into the pie crust.
Drizzle in the caramel ice cream topping and stir gently. You don't want to incorporate the caramel completely, you want to have ribbons of it running through each slice of pie!
Scoop the ice cream mixture into the cookie crumb crust. Press it down gently, to make sure the ice cream settles into the crust and there are no air pockets.
Place the pie in the freezer for at least 3 hours, or until it's completely frozen.
Top slices with more caramel just before serving, if desired.