Pour milk into a large container or bowl with a pouring spout. Stir in sweetened condensed milk and vanilla.
Stir in cheesecake pudding mix and whisk to incorporate.
Warm caramel for 30 seconds in the microwave until it has softened enough to easily stir.
Pour caramel into milk mixture and stir to combine. Place mixture in the refrigerator for 4-6 hours to thoroughly chill.
Follow instructions for churning on your ice cream maker. If using Kitchen Aid attachment, make sure you freeze the mixing bowl for 15 hours before use. Attach bowl and churning blade to mixer, lock in place and set mixer to low speed, #1.
As frozen bowl turns carefully pour in the chilled milk mixture. Mix until ice cream is in a soft serve stage, about 20 minutes. Place ice cream into a freezer container and freeze for 4-6 hours before serving.