Despite the demonstrated importance of customer sentiment in social media for outcomes such as purchase behavior and of firms’ increasing use of customer engagement initiatives, surprisingly few studies have investigated firms’ ability to influence the sentiment of customers’ digital engagement. Many firms track buyers’ offline interactions, design online content to coincide with customers’ experiences, and face varied performance during events, enabling the modification of marketer-generated content to correspond to the event outcomes. This study examines the role of firms’ social media engagement initiatives surrounding customers’ experiential interaction events in influencing the sentiment of customers’ digital engagement. Results indicate that marketers can influence the sentiment of customers’ digital engagement beyond their performance during customers’ interactions, and for unfavorable event outcomes, informational marketer-generated content, more so than emotional content, can enhance customer sentiment. This study also highlights sentiment’s role as a leading indicator for customer lifetime value.