Preheat your oven to 400°F. While it heats, trim about 1 inch from the bottom of the asparagus spears and pat them dry with paper towels—this removes excess moisture so they cook properly and the pastry stays crispy. Shred the gouda cheese and grate the parmesan, then combine them in a bowl. In a small bowl, mix together the salt, pepper, and garlic powder. Having everything prepped and ready before cooking ensures a smooth assembly process.
Arrange bacon strips on a baking rack set over a sheet pan and place in the preheated 400°F oven. Bake for 18-20 minutes until the bacon is crispy but still pliable enough to wrap (it should bend without breaking). Remove from the oven and pat the bacon dry with paper towels to remove excess grease. Once cool enough to handle, chop each bacon strip in half. I like to use center-cut bacon because it has less fat and crisps up more evenly than thick-cut varieties.
Unroll the crescent roll dough and lay it flat on a clean work surface. Cut the dough into 20 triangular pieces (roughly the size of the original crescent rolls, one per bundle). Brush each triangle lightly with olive oil, then sprinkle with a pinch of the seasoning mixture from Step 1. Place one piece of bacon and 2-4 asparagus spears on each triangle, arranging them so they point toward the tip of the triangle. Sprinkle about a tablespoon of the cheese mixture over the filling on each bundle.
Fold the corners of each dough triangle up and over the filling, creating a bundle with the asparagus tips poking out slightly at the top. Gently press the seams together so the dough stays folded. Place all bundles on a parchment-lined baking sheet, spacing them about an inch apart. Drizzle lightly with a bit more olive oil, then top each bundle with another small sprinkle of the remaining cheese mixture and a tiny pinch of the seasoning. I find that the exposed asparagus tips will caramelize beautifully during baking, adding a nice charred edge to each bundle.
Place the baking sheet in the preheated 400°F oven and bake for 12 minutes until the pastry is golden brown and puffed. The edges of the dough should be crispy and the cheese will have melted slightly over the filling. Remove from the oven and let cool for 1-2 minutes before serving warm. These bundles are best enjoyed immediately while the pastry is still crispy and the cheese is melty.