Improvements in a compliant upright drink insulator attachment device that is works with a standard drink insulator. The attachment device uses two parts where one part mates with the second part to slip through a standard insulated drink holder. These insulated drink holders are commonly called coolies or koozies and are manufactured with a central hole to allow for draining. A clip connects a compliant cord to one or both of the two parts. The compliant cord is configured as a coiled cord. A weight is connected to the free end of the compliant cord to keep the insulated drink holder in an upright orientation in the water. The compliant cord allows the weight to move semi independent from the insulated drink holder, and further allows the weight to be stored within the insulated drink holder for storage when it is not being used.