Information technology (IT) service providers that offer both customized and routinized IT services (help-desk services, software services, business process outsourcing, consulting services) are often advised to consider moving up or down the value chain. Such advice is couched in language that emphasizes the revenue possibilities that exist higher up the value chain (moving from software outsourcing to packaged software, for instance) or volume that exists lower down in the value chain. However, the reality for firms that have attempted such moves is more ambiguous—many highly successful service providers have tried to move out of their niche and failed. Why? We address this question of why service providers may fail when they move up or down the value chain using agent-based modeling. We create a set of representative IT service firms, endow them with different types of resources and capabilities, and model the profitability implications of moves up and down the value chain in the presence of competitors. We run a series of simulations using these representative firms to see when such moves along the value chain are likely to be successful and when they are not. We find that firms moving up the value chain are successful only when such moves are accompanied by significant resource changes. In contrast, firms moving down the value chain are likely to be successful only if such moves are accompanied by learning capability arising out of higher absorptive capacity. Not surprisingly, we find that moves along with the value chain without significant investments in resources and capabilities, for the most part, end in failure.