Crisp up the phyllo cups. Preheat the oven to 350°F. Arrange the phyllo cups on a rimmed baking sheet and bake until just crispy, for 5 to 6 minutes. Remove from the oven and allow cups to cool completely on the sheet tray.
Prep the vegetables. Remove the fronds from fennel bulbs and set aside for garnish. Finely mince the fennel bulbs, shallot or onion, and garlic. Aim for very small pieces here, about 1/8-inch squares. If you prefer, you can lightly pulse the vegetables in a food processor, taking care not to turn them into a paste.
Cook the filling. In a large skillet over medium heat, warm the olive oil until the surface just begins to shimmer. Add the minced vegetables and kosher salt. Sauté vegetables, stirring occasionally, until translucent and soft, about 10 minutes. Lower heat if they begin to brown.
Assemble the filling. When vegetables are tender, remove from heat and stir in chopped olives, orange zest and red pepper flakes (if using). Taste mixture and add more salt if necessary. Set aside to cool to room temperature, about 20 minutes.
Whip the goat cheese. While the vegetable mixture is cooling, place the softened chevre and honey in a medium bowl. Squeeze in the juice of half the zested orange. Using a hand mixer, whip the goat cheese mixture until thoroughly combined. Taste and add a pinch of kosher salt if needed.
Assemble the phyllo cups. Scoop 1 tablespoon of room temperature vegetable mixture into each phyllo cup. Gently transfer filled cups to serving platter to garnish.
Add whipped goat cheese. If you’re feeling fancy, scrape goat cheese mixture into a piping bag fitted with a small star tip. You can also use a plastic bag with an end snipped off. Either pipe or spoon a small dollop of whipped goat cheese onto each filled phyllo cup.
Garnish and serve. Roughly chop reserved fennel fronds and place on top of goat cheese dollop for a garnish. Serve immediately.
Notes
Shop this recipe: Visit our shopto browse quality Mediterranean ingredients, including the olive oil and honeyused in this recipe.
Make ahead: The vegetable mixture and the whipped chevre can be made and refrigerated up to three days ahead. Allow both to come to room temperature before crisping up and filling phyllo cups.
Serve Immediately: Once assembled, the phyllo shells absorb moisture from the filling quickly. They'll get soggy if they sit too long, so it's best to serve them quickly!