regular-cut bacon (any flavor/smoke preference, such as peppered, hickory-smoked, maple flavored, etc, but I would recommend not using thick-cut as it will be too heavy and big for the delicate phyllo cups), cut in half cross-wise
maple syrup (I used pancake maple syrup, but real deal syrup will work)Preheat oven to 350 degrees F. Line a rimmed baking sheet with parchment and lightly grease it with cooking spray. Place the phyllo cups onto the baking sheet and set aside briefly.
the bacon in batches in a large skillet, cooking until the bacon is just about done but not crispy. The bacon should be on the chewier side, as it will continue to cook more as you bake it. Drain the bacon onto a paper towel-lined plate and let cool briefly before chopping into tiny bits.
a ½ tsp of brown sugar into each phyllo cup and add a small squirt of maple syrup on top. Fill past the brim of the phyllo cup with bacon, mounding it into the cup. Sprinkle with the remaining brown sugar.
for approx. 12-15 minutes or until the phyllo cups and bacon are crisp and the maple caramel is bubbly and caramelized. Cool for about 5 minutes before serving.