Heat 2 inches of vegetable oil in a large Dutch oven to 315 degrees F. Have a cooling rack set over a paper towel-lined baking sheet ready.
Combine the strawberries and sugar in a large bowl and toss well. Set aside to macerate at room temperature.
Separate a biscuit and stretch it slightly into an oblong shape. Starting on the short end, tuck and roll into a 5-inch-long log. Repeat with the remaining biscuits. Working in 2 batches, fry the biscuits until they are golden brown and cooked through, about 5 minutes per batch. Drain on the cooling rack.
Drain the berries, reserving the liquid in the bowl (you should have about 3 tablespoons of liquid). Whisk the cream and vanilla in an electric mixer on medium-high speed until foamy. Add the reserved berry liquid and whip to soft peaks. Set aside.
To assemble, split the fried biscuits into 2 pieces lengthwise with a serrated knife. Set the bottom halves on a platter and top the halves with the strawberries. Top with the whipped cream.
Place the fudge sauce in a microwave-safe bowl. Microwave on high until in 15-second increments, stirring in between, until the sauce is warm and becomes thin. Dip the tops of the other halves in the warm fudge sauce. The sauce should be loose enough to coat the tops easily; if it's not, reheat it and, if necessary, thin it out with a little canola or vegetable oi). Set the dipped tops over the whipped cream.