Preheat oven to 375° F. Lightly spray 2 ramekins with nonstick cooking spray. Place ramekins on a baking sheet.
Chop strawberries and toss with 1 tsp for sugar. Divide equally between the two ramekins.
In a small bowl, mix together flour, sugar, baking powder, and salt until well combined. Mix in butter with a fork or your fingers until crumbly. Stir in milk and vanilla until just combined. Spoon over top of the strawberries.
Bake cobblers for about 22-25 minutes until the cobbler is set and lightly brown. You will likely see strawberry juice bubbling up around the edges of the cobbler.
Cool until warm or room temperature then top with a dollop of whipped topping.