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Combine the stroop, brown sugar, butter, cinnamon and salt in a small saucepan. Cook over medium heat until the sugar and butter are melted and the mix just comes to a boil. Transfer the filling to a bowl and set aside to cool.
Combine the milk and yeast in the bowl of a stand mixer or in a large mixing bowl. Use the beater and mix until the yeast is dissolved. Add the eggs, melted butter and sugar.
With the mixer running on low, add the cinnamon and salt. Add the flour and mix until most of the flour is incorporated. Turn the dough out into a lightly floured surface and knead into a ball. The dough is quite soft.
Divide the dough into 18 pieces, each piece should weigh about 50g. Roll each piece to a ball and line them up on a sheet pan. Cover with plastic wrap and set the dough aside for 1 hour.
Preheat the waffle iron. Take a ball of dough and flatten it to a disc. Place it on the waffle iron and close the iron.
Bake until golden brown, about 2-3 minutes. Use a fork to lift the waffle off the iron. Immediately use a knife with a thin sharp blade to split and open up the waffle. Generously spread the inside of the waffle with stroop (about a tablespoon) and sandwich the two halves together. Continue with the remaining dough.