Today, Generation Y represents the largest demographic group in America and is defined by an Internet landscape that has revolutionized daily living. Likewise, social media has revolutionized the public relations industry. This research longitudinally examines Generation Y’s expectations of organizational social media use across three years and directly compares results to longitudinal research that analyzes public relations professionals’ own indications of organizational social media use across three years. Results indicate that organizational communication via social media generally fails to meet the expectations of the Generation Y demographic; however, professionals’ indications of what should be happening are more closely aligned. Implications for scholarship and practice are discussed.