The e-mail system at Monte Cassino School in Tulsa, Oklahoma, is more than just e-mail. It is the cornerstone of an evolving, collaborative online community the preK-8 Catholic school relies on to involve parents in their children's education. When the system was hit six years ago by a major virus attack, the school turned to a Cupertino, California-based IT security vendor, Symantec, for its well-known anti-virus solutions. Monte Cassino is just one example of the growing number of schools that have decided to outsource various combinations of their infrastructure/application management to cope with increasingly challenging IT environments. Third-party IT systems management companies come in two basic flavors: managed service providers (MSPs), which focus on an organization's software infrastructure; and application service providers (ASPs), which address the application layer. The advantages of outsourcing IT systems management services are clear. One of the chief benefits is that third-party providers tend to have the cutting-edge expertise to support elaborate, sophisticated IT environments that most districts cannot maintain. Outsourcing can also help to even out a funding and expenditure stream. School administrators should seriously consider both service alternatives (MSPs and ASPs), because they have matured to the point where they can be leveraged and taken advantage of with far less risk than back in the dot-com era.