Unfavorable contractual agreements can be detrimental to the well-being of an organization. The objective of this paper is to examine the acquisition of enterprise software and the perceived importance of various key/critical contractual issues by IT managers within both the manufacturing and service industries. Often software contracts are written to favor the vendor and their terminology is vague and in a high-level language that can make organizations vulnerable. Among all IT applications, enterprise software is particularly critical due to integrating various critical business processes. In addition, ES implementations are among the most expensive types of IT implementations. Thus, enterprise software contracting mistakes can be particularly costly for organizations. Our results through exploratory analysis indicate that rights (right to assign and re-assign, or port the software license), contractual assurance, and responsibilities, indemnities and warranties are among the most important issues while purchasing enterprise software.