Warm the milk until lukewarm, then crumble in the yeast and add a teaspoon of sugar. Let it sit for 5-10 minutes until foamy.
In a large bowl, combine the flour, remaining sugar, and a pinch of salt. Create a well in the center.
Crack the egg into the well, then add the proofed yeast mixture. Begin mixing with a wooden spoon or using a stand mixer with the dough hook attachment.
Slowly incorporate the softened butter, then add the pearl sugar. Knead the dough until it is smooth and elastic, about 5-7 minutes.
Cover the dough with a clean kitchen towel and let it rise in a warm place for 45-60 minutes, or until doubled in size.
Preheat your waffle iron and lightly grease the plates with butter. Scoop a portion of the dough onto the iron and cook until golden brown, about 3-4 minutes.
Before serving, top the hot waffles with sliced Black Forest ham, grated cheddar cheese, and fresh arugula. Serve immediately!
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