Step 1: Prepare the filling: In a medium bowl, beat the softened cream cheese, powdered sugar, and vanilla until smooth and fluffy. Fold in the 6 crushed Oreos. Cover and refrigerate for at least 15 minutes to firm up—this prevents leakage during frying.
Step 2: Prep the dough: Open the biscuit can and separate the rounds. On a lightly floured surface, gently stretch or roll each biscuit into a 5- to 6-inch circle (about ⅛-inch thick). Avoid tearing.
Step 3: Assemble the bites: Place 1 heaping tablespoon of chilled cheesecake filling in the center of each dough circle. Top with half an Oreo cookie (or a small chunk if using mini Oreos). Carefully gather the edges of the dough up and over the filling, pinching firmly to seal completely. Smooth any seams and shape into a ball or slightly flattened sphere. Repeat with remaining biscuits.
Step 4: Heat the oil: In a deep skillet or Dutch oven, heat 2–3 inches of oil to 350°F (175°C). Use a candy or deep-fry thermometer for accuracy—maintaining this temperature is key to golden, non-greasy bites.
Step 5: Fry in batches: Carefully lower 2–3 assembled bites into the hot oil (do not overcrowd). Fry for 2–3 minutes per side, turning once, until deeply golden brown and puffed. Remove with a slotted spoon and drain on a wire rack set over paper towels.
Step 6: Make the glaze: While the bites cool slightly, whisk together powdered sugar, 1 teaspoon milk, and vanilla. Add more milk drop by drop if needed to reach a thick but drizzle-able consistency.
Step 7: Finish and serve: Drizzle warm bites with glaze and immediately roll or sprinkle with the reserved 1 cup of crushed Oreos. Serve warm for the best texture and flavor.