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Toss chocolate chips, ancho chile pepper and cinnamon in small bowl. Set aside.
Stem and core strawberries. Fill each strawberry with 1/2 teaspoon chocolate chips and 2 to 3 marshmallows. Place strawberries in jalapeño popper tray.
Grill over medium-high heat 5 minutes or until strawberries are warmed and marshmallows are toasted. Sprinkle with additional cinnamon, if desired.