Advancing digital collaboration and fostering effective communication among a widespread workforce continues to be a perpetual challenge for companies. Organizations are progressively turning to Enterprise Social Media (ESM) because they promise new  avenues for collaborative working. However, most ESMs fail to reach a wider adoption by the workforce, owing to an underutilization by the employees. To enhance the understanding of the underutilization phenomenon, we use affordance actualization theory as our theoretical lens to critically study the challenges employees face in their attempt to actualize respective ESM affordances. By analyzing comments from 992 frequent, infrequent, and discontinued ESM users from a large multinational company, we uncover four major challenges. By enhancing our understanding of ESM affordances and by incorporating the full spectrum from problem identification to solution, we provide practical advice for digital leaders and meaningful theoretical implications for the IS community.