Heat waffle iron and combine sugar and cinnamon in a small bowl.

Brush butter on one side of each flatbread and sprinkle sugar mixture on top. Place flatbreads, one at a time, sugar-side down on the waffle iron. Brush other side with butter and sprinkle with sugar. Close waffle iron and cook until golden and sugar has melted, about 3-4 minutes.

Remove and gently fold in half, being careful not to tear or crack the middle. Let cool and repeat with remaining flatbreads.

Fill flatbreads with ice cream. The easiest way to do this is to cut through the pint of ice cream into 4 equal circles with a serrated knife. Remove the cardboard and place each circle inside the folded flatbread. Freeze until completely hard, at least 1 hour.

Melt chocolate chips over a simmering water bath or in the microwave. Dip each sandwich halfway in the chocolate. Return to freezer to harden.

Enjoy immediately or wrap in plastic wrap and freeze for up to 1 week.