Heat waffle iron according to manufacturer's instructions.
Spray with a non-stick cooking spray.
Pour the waffle batter onto the waffle iron as you would for normal waffles. Let the waffle batter cook until it is solid, but not brown or crispy. In my waffle iron, this took two minutes.
Leaving the waffle on the waffle iron, fill each depression in the waffle with brown sugar.
Place a pineapple ring in the center of each waffle section.
Spread a little brown sugar on top of the pineapple ring.
Close waffle iron and cook until sugar starts to caramelize. This took four minutes in my waffle iron.
Eat while still hot. We found these sweet enough to eat without syrup, but if you want to add some, go for it!