Step 1: Prepare the Asparagus

First, prepare your asparagus spears. Wash them thoroughly under cool water and pat them completely dry. A dry surface is crucial for getting a good char on the grill. Hold a spear at both ends and bend it gently. It will naturally snap at the point where the tender part meets the tough, woody base. Discard the woody ends. Repeat with the remaining spears. Place the trimmed asparagus in a large bowl, drizzle with 1 tablespoon of olive oil, and sprinkle generously with kosher salt and black pepper. Toss gently to ensure each spear is lightly coated.

Step 2: Grill the Asparagus

Preheat your grill (gas or charcoal) to medium-high heat. You want it hot enough to create char marks quickly without turning the asparagus to mush. Place the seasoned asparagus spears directly on the grill grates, perpendicular to the bars to prevent them from falling through. Grill for about 3 to 5 minutes, turning them occasionally with tongs, until they are tender-crisp and have beautiful char marks. You are not trying to cook them all the way through at this stage, as they will cook further in the oven. The goal is to get that smoky, grilled flavor. Once grilled, remove the asparagus from the grill and set them aside on a plate to cool slightly.

Step 3: Prepare Your Phyllo Workstation

Working with phyllo dough can seem intimidating, but the key is preparation and speed. Before you unroll the dough, have everything ready: your melted butter in a bowl with a pastry brush, your grated Parmesan cheese mixed with the garlic powder, salt, and pepper, and a clean, large work surface like a cutting board or countertop. Unroll the phyllo dough sheets. Immediately cover the stack of dough with a piece of plastic wrap, and then place a clean, damp kitchen towel over the plastic wrap. This is the most critical step to prevent the delicate sheets from drying out and becoming brittle.

Step 4: Assemble the Bundles

Preheat your oven to 375°F (190°C). Line a large baking sheet with parchment paper. Take one sheet of phyllo dough from the stack and place it on your work surface, keeping the rest covered. Using your pastry brush, lightly brush the entire surface of the phyllo sheet with melted butter. Don’t drench it; a light, even coat is perfect. Sprinkle about a tablespoon of the Parmesan cheese mixture evenly over the buttered sheet.

Place a second sheet of phyllo directly on top of the first one, aligning the edges. Brush this second sheet with melted butter as well. Using a sharp knife or a pizza cutter, cut the layered phyllo stack lengthwise into four long, equal strips.

Step 5: Wrap the Asparagus

Take one grilled asparagus spear. If you are using the optional cured ham, wrap a thin slice snugly around the middle of the spear first. Place the spear at the bottom end of one of the phyllo strips. Begin to roll the asparagus up in the phyllo strip, rolling it on a slight diagonal to create a beautiful spiral pattern. Continue rolling until the entire spear is encased in the crispy phyllo. Place the finished bundle seam-side down on the prepared baking sheet. Repeat this process with the remaining asparagus spears and phyllo strips until all are wrapped.

Step 6: Bake to Golden Perfection

Arrange the phyllo-wrapped asparagus on the baking sheet, ensuring they have a little space between them so they can crisp up on all sides. Give the tops of each bundle a final, light brush of melted butter. This will ensure they bake to a deep, golden-brown color. Bake in the preheated oven for 12 to 18 minutes, or until the phyllo is golden brown, crispy, and looks beautifully flaky. Keep a close eye on them in the last few minutes, as phyllo can go from golden to burnt very quickly.

Step 7: Cool and Serve

Once baked, remove the baking sheet from the oven. Let the asparagus bundles cool on the pan for a few minutes. This allows the phyllo to set and achieve its maximum crispness. Serve warm.