A vacuum cup for a material handling system includes a body portion and a perimeter seal that functions to substantially seal against an object. The vacuum cup may transport the object when a partial vacuum is applied to the vacuum cup to retain the cup to the object. The vacuum cup includes a relief port and sealing member that function to at least partially relieve the vacuum from the vacuum cup to allow the vacuum cup to be detached from the object with a reduced force, even while the vacuum is applied. The sealing member may engage a surface of the object to close the relief port. When the vacuum cup is initially pulled or moved away from the object, the sealing member is at least partially separated from the object and allows the cavity to be vented to at least partially relieve the vacuum within the cavity.