1. Preheat oven to 350 degrees F.
2. Heat 1 TBS olive oil on medium-low and add sliced onions, salt, and pepper. Cook onions, stirring occasionally, until they’ve softened and appear medium-dark brown in color and caramelized, about 30 minutes. Add dried rosemary and stir.
3. Spray 12-cup muffin pan with non-stick cooking spray. One by one, fold each phyllo sheet in half once and then in half again (should now be 4 layers thick). Press folded square of phyllo into muffin cup to form phyllo dough cup. Repeat with remaining 11 sheets of phyllo. Spray each phyllo cup with non-stick cooking spray.
4. Distribute cubed pear and goat cheese crumbles among 12 cups. Drizzle honey over the cheese. Once onions have caramelized, distribute them over the goat cheese, pear, and honey.
5. Bake in oven for 15 minutes until phyllo dough has turned light brown and goat cheese has melted. Remove phyllo cups from muffin pan and let cool on wire rack for 5 minutes. Serve warm.