Preheat oven to 375 degrees. Spray a 9-inch tart pan with a removable bottom with cooking spray.
Place the pie crust in the prepared tart pan and fold the excess down into the pan and press it into the rim of the tart pan to form a neat crust. Place on a baking sheet.
Place a piece of parchment paper over the dough and fill with pie weights. Bake for 18 to 20 minutes or until the crust is baked but not browned. Transfer to a cooling rack to cool.
Meanwhile, heat a nonstick skillet over medium-high heat. Add the prosciutto, reduce heat to medium and cook 2 to 3 minutes or until any fat is rendered off and the prosciutto is just lightly browned but not crisp. Transfer to a plate to cool.
Heat olive oil in the skillet over medium-high heat. Add the shallot, reduce heat to medium and cook for 2 to 3 minutes or until beginning to soften. Add the cut (halved) asparagus and stir-fry for 30 seconds. Add 1 tablespoon water and continue cooking for 1 more minute or until the water has evaporated and asparagus is bright green. Season with a pinch of salt and black pepper. Remove from heat and allow to cool.
Sprinkle Parmesan cheese over the bottom of the baked crust.
Combine prosciutto, asparagus and Fontina cheese (either in the skillet used to cook everything after it has cooled or in a bowl). Transfer to the prepared crust and evenly distribute everything, pressing it down into the crust so the top is level.
Whisk together eggs and half-and-half (or milk). Season with 1/4 teaspoon salt and black pepper. Pour custard mixture over asparagus mixture. Top with the 5 raw pieces of asparagus.
Bake at 375 degrees for 10 minutes. Reduce heat to 350 degrees. Bake another 30 to 40 minutes or until set and top is just beginning to brown.
Let cool in the pan for 10 minutes. Remove the pan sides and cut into wedges. Serve hot, warm or room temperature.