Nutrition per serving may change if servings are adjusted.
½ cup plus 1 tablespoon sugar, divided
¼ cup plus 1 teaspoon water, divided
¼ cup nonfat evaporated milk
1½ teaspoons frozen orange-juice concentrate
4 ripe pears, preferably Bosc or Anjou
½ cup fresh orange juice
3 tablespoons sliced almonds, toasted
3 sheets phyllo dough, thawed overnight in refrigerator
1½ teaspoons butter
1 tablespoon canola oil
To make the caramel sauce: Combine ½ cup sugar and ¼ cup water in a heavy saucepan. Bring to a boil over medium-high heat, stirring to dissolve the sugar. Cook, without stirring, until it turns a deep amber color, about 5 to 8 minutes. Do not burn.
Remove from heat and carefully swirl in the remaining 1 teaspoon water to stop the cooking: be careful, it will spatter. Let cool 2 minutes, then gradually stir in evaporated milk. Return the pan to low heat and stir to dissolve caramel: the mixture should not boil. Remove from heat and stir in orange-juice concentrate.
To bake the pears: Preheat oven to 375°F.
Peel, halve and core pears. Place in a large round baking dish or pie plate, with stem-ends toward the center. Pour orange juice over pears. Cover with foil and bake for 30 minutes. Uncover and sprinkle with remaining 1 tablespoon sugar. Bake until pears are tender and the juice is reduced to a glaze, basting from time to time with juice, 20 to 30 minutes more. Set aside.
To make the nests: Cut each sheet of phyllo into 4 squares. Stack the squares and cover with plastic wrap. Set aside.
Melt butter in a small saucepan and stir in oil. Brush four 1¼-cup custard cups lightly with the butter-oil mixture. Place one phyllo square in the bottom of a custard cup and brush lightly with butter-oil mixture. Set another square on top at an angle to the first, brush as well. Repeat with the third phyllo square. Fill remaining custard cups in the same manner. Set the cups on a baking sheet and bake in a 375°F oven until crisp and golden, 7 to 10 minutes.
To serve, gently lift each phyllo nest out onto a dessert plate. Set two pear halves in each nest, spoon on a generous spoonful of caramel sauce and sprinkle with the toasted almonds.
Make Ahead Tip: Cover and refrigerate the sauce (Steps 1-2) for up to a week. Bring to room temperature before serving.