Open the can of pre-made cinnamon rolls and separate each individual roll, placing them all on a piece of parchment paper.
Lay another layer of parchment paper over the top and press down on each roll, flattening it to about half its height. By doing so, it is easier to create equally sized waffle rolls, then simply smashing them in the waffle iron.
Warm up your waffle iron and coat the each side of the press with some cooking oil.
Place one of the smashed cinnamon rolls in the press and cook it in the iron for about 2 minutes or until the roll is fully cooked. Don't smash the roll further during this process. Also, if the rolls are sticking, maybe brush them with a bit of oil. Because they are "rolled" then like to unravel.
Place all cooked rolls in the fridge for 30 minutes to fully cool them down.
Pair the waffle rolls by size and then place a heaping scoop of vanilla ice cream onto half of them.
Using a spoon, smash down the ice cream, spreading it throughout the waffle cinnamon roll. Top with another roll.
Place the ice cream sandwiches in the freezer at least for 30 minutes before serving.