Place ice cream in refrigerator for about 30 minutes or until slightly softened. Gently stir in pepper. Place in freezer until firm.
To make Port Syrup:
In saucepan, simmer port and sugar until reduced to 1/3 cup. Chill.
To make Cocoa Wafers:
Cream sugar and butter. Mix in cocoa, vanilla and salt; when smooth, mix in flour just until incorporated. If needed, add up to 2 teaspoons of water to make firm but pliable dough.
Form dough into a flat disc between 2 pieces of plastic wrap; chill.
Roll chilled dough between 2 pieces of plastic wrap to 3/8-inch thickness. With sharp knife or cookie cutter, cut into leaf shapes about 3 inches long. Place on parchment-lined sheet pan. Bake in 325°F oven 10 to 12 minutes or just until set; wafers will firm as they cool.
To grill strawberries:
Strip leaves from rosemary skewers, leaving 2 to 3 inches of leaves at the top. Thread 4 strawberries halves onto each skewer.
Grill skewers, cut sides down, about 4 minutes or until grill marks form.
For each serving, place one 1/2-cup scoop Black Pepper Ice Cream in chilled glass; spear 2 skewers into ice cream. Spoon 1 tablespoon Port Syrup onto ice cream. Garnish with 2 Cocoa Wafers.