01 - Place whole milk, softened cream cheese, vanilla ice cream, hulled strawberries, granulated sugar, and vanilla extract into a blender canister.
02 - Blend on high speed until completely smooth and creamy, stopping to scrape down the sides of the blender as needed to ensure even incorporation.
03 - Taste the milkshake and add additional sugar if desired, blending briefly to incorporate.
04 - Pour the completed milkshake evenly into two chilled glasses.
05 - Top each glass with whipped cream, crushed graham crackers, and fresh strawberry slices as desired.
06 - Serve immediately with straws while the milkshake is at peak freshness and temperature.