Long-term unengaged email addresses can become a headache for executives, especially when it comes time to address deliverability issues. The problem often escalates because organizations delay removing these contacts until the list has ballooned. This not only complicates the conversation with management but can also harm overall email performance. To tackle this, the article emphasizes the importance of automating reengagement efforts and sunset policies. To reengage old contacts effectively, the author suggests a simple two-step setup. First, implement a Subscriber lifecycle automation that checks in at key intervals: 90, 180, 270, and 365 days. This allows marketers to identify potential churn points and personalize their outreach accordingly. Second, establish a Sunset Policy that automatically unsubscribes contacts who show no signs of engagement after a specified period. This proactive approach helps maintain a healthier email list and improves deliverability without overwhelming team resources. Examples from Ortto illustrate how these tools can be integrated into marketing systems. By automating these processes, marketers can focus on engaging active subscribers while managing unengaged contacts systematically. With this strategy, the pressure on management discussions decreases, and the risk of deliverability issues diminishes significantly.