Roll out all the pie crusts and using a large circle cutter, cut out 4-5 circles in each pie dough so you should have a total of 16-20 circles.
Set half of the circles on the tray.
Place the apple pie filling in a large bowl and add in the vanilla extract. Using two knives, cut the apple pie filling into small pieces.
Scoop the filling into the center of all the circles on the tray. You might not use all the filling, but close.
Place the remaining circles of dough on top of the apple filling and crimp the edges securely using the tines of a fork.
Brush the melted butter evenly over all the finished pies
Toss together the brown sugar and cinnamon and sprinkle that mixture on top of the melted butter.
Bake in the preheated oven until pies are a very light golden brown and filling is bubbling, 20 to 30 minutes.
Remove from the oven. Whisk together the powdered sugar, maple syrup, and milk as needed (add slowly and increase if needed) until a very thick frosting is formed.
While the pies are still warm (not hot), drizzle this mixture generously over the pies.
Allow to cool.
Dip the pies into the caramel sauce and enjoy!
Notes
*This will be 4 total pie crusts because each package has 2 crusts in it