Chill two tall glasses in the freezer while you prep.
Blend the milk, chocolate syrup, and vanilla extract on low until combined.
Add the softened ice cream and salt. Blend on medium until smooth and thick.
Pulse in most of the crushed cookies until just mixed, leaving small bits for texture.
Pour into chilled glasses. Top with whipped cream and a sprinkle of cookie crumbs.
Notes
For a thicker shake, use a bit less milk or freeze the glasses longer. Try a minty twist with a drop of peppermint extract, or blend in a spoonful of peanut butter for extra richness. Best served immediately; freeze leftovers in popsicle molds for a quick dessert.This recipe is an original creation inspired by classic Oreo Milkshake Bliss flavors. All ingredient ratios and instructions are independently developed.