Abstract: Provided is a system that enables a computer user to purchase and maintain installed operating systems and applications. Also provided is a method and system that detects and installs updates to programs and operating systems (OSs) on a computing system and ensures that the upgrades are compatible with existing software. A method is provided wherein a computer environment is scanned for all installed software and supporting files and logic such as libraries and OSs. A detected configuration is transmitted to a service provider who generates a service and support plan. The plan is offered to the administrator of the computer environment as an alternative to vendor-supplied plans. Thus, an administrator of a particular computing environment is able to centralize the maintenance and upgrade of installed software. The claimed technology provides access to a single-source pricing and support structure and enables the service provider to negotiate and purchase bulk upgrade packages.