Preheat oven to 400°F.
Prepare potatoes: Toss potatoes with olive oil, garlic powder, paprika, thyme, salt, and pepper. Spread on one side of a large sheet pan.
Roast potatoes for 20 minutes.
Make the glaze: Whisk together brown sugar, pineapple juice, mustard, honey, melted butter, garlic powder, and black pepper.
Add ham: Remove pan from oven. Arrange ham slices on the open side of the pan, slightly overlapping. Top with pineapple slices. Brush generously with glaze.
Bake for 15 minutes.
Add asparagus: Toss asparagus with olive oil, salt, and pepper. Remove pan, add asparagus, and brush ham with remaining glaze.
Return to oven and bake 10–12 minutes, until potatoes are fork-tender, asparagus is crisp-tender, and ham is heated through.
Optional: Broil for 1–2 minutes for extra caramelization.
Serve immediately, finishing asparagus with lemon juice or Parmesan if desired.