In blender, place milk, 1 heaping tablespoon strawberry preserves and 2 to 3 baked cookies. Cover; blend about 30 seconds until smooth.
Add ice cream; blend again until milkshake is well blended.
Drizzle additional strawberry preserves down inner wall of 1 large cup or 4 individual cups. Fill cup or cups with milkshake. If using large cup, add 4 straws.