Organizations responding to business challenges have long been concerned about the technologies they are using and the contributions of these technologies to their ability to make the necessary changes quickly and effectively. This dissertation posits that the relationship between the Information Systems (IS) group and the business is also of concern to organizations responding to business challenges. In addition, a new way of classifying challenges is outlined, suggesting that both equivocality and stakeholder complexity of the business challenge predict whether there will be successful systems agility. An empirical study involving 131 IS and business managers confirms that the IS to business relationship, equivocality, and stakeholder complexity make a difference in systems agility success, with interesting results regarding the moderating effect of relational capital in equivocal agility challenges.