Place your air popped popcorn in large bowl.
Preheat oven to 250 degrees and line a large rimmed baking sheet with parchment paper
Place all ingredients EXCEPT baking soda and flavoring (and popcorn!) in small saucepan.
Bring saucepan to a boil, stirring constantly.
Continue to let your candied sauce boil, stirring occasionally until a candy thermometer reads 250. THIS IS SUPER IMPORTANT.
Remove from heat and quickly stir in baking soda and cherry flavoring.
Pour over popcorn in bowl and stir really well until popcorn is coating.
Place on prepared baking pan.
Cook for 30 minutes stirring after 15 minutes.
Cool on parchment covered wire racks.
Sprinkle chocolate chips over popcorn.