Health plans offering Medicare recipients supplemental insurance serve an over-65 population challenged to manage a complicated mix of government and private coverage. Currently, plans have the trust of this Medicare group, but consumers with supplemental insurance are not getting what they need from associated online channels. Without necessary changes, consumers' trust will wane, and with a wave of older boomers retiring and entering this market, health plans' retention risk will only rise. The time for usability repairs is now.