Pineapple upside down waffles were born out of my mom’s request for pineapple upside down cake and my desire to make something a little more unique. I first experimented with throwing pineapple upside cake batter on the waffle iron. This was a fail – batter stuck to the iron and the waffles fell apart in my hand. I eventually settled on a technique involving regular waffle batter, brown sugar, and pineapple rings.
I love how the pineapple rings totally merge with the waffle batter in these pineapple upside down waffles. What I love even more is the pineapple upside down cake flavor the waffles take on when pineapple juice spills onto brown sugar-covered waffle batter.
Although Jonathan claims that all pineapple upside down cakes have maraschino cherries, my mom’s cakes never did so I left them off. If you must include them, I’d add the cherries after the fact as a garnish.
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If you like this idea, I bet you’d also like my waffle iron baked apples. You could even try using apples instead of pineapple in upside down waffles!