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A large number of IT employees will soon be leaving the workforce due to retirement, which presents a serious problem for many IT departments. This problem is of greater concern in organizations and industries with complex business practices, legacy systems, or greater proportions of older workers. These organizations are vulnerable to a phenomenon called Y2Gray. This article explores Y2Gray by explaining the problem, identifying organizations at risk, and presenting recommendations to address this problem. The authors share their findings from interviews with two firms that are coping with Y2Gray.