Make glaze by whisking together black pepper, brown sugar, balsamic vinegar and preserves.
Line a baking sheet with foil. Top with an oven-safe cooling rack and spread bacon out on rack. Transfer bacon to oven and bake until nearly crisp, 20 to 25 minutes.
When bacon is nearly finished, remove from oven and brush with glaze. Return to oven and continue baking until crisp and caramelized, 5 to 7 minutes more.
While bacon finishes, slice sandwich rolls in half. Place rolls, cut-side up on a second sheet pan. Spread one side of each roll with brie and toast in the oven until brie is melted and roll is golden brown.
Toss arugula with olive oil and season with some salt and black pepper.
Heat cooking oil in a skillet. Crack eggs into heated oil and fry until cooked to your liking (I like them sunny-side up).
Assemble sandwiches by topping the melted brie side of the sandwich roll with bacon, arugula and a fried egg.