The present invention interrogates computer systems prior to software installations to ensure software installations operate correctly and do not conflict with existing hardware and software. An agent application is first installed on a user's system. When a new program is about to be installed on the user's system, the agent checks if certain prerequisite requirements are met. The prerequisite requirements are downloaded from an expert system library, and the agent interrogates the user's system to determine if it passes the downloaded requirements. If the system passes, then the software is installed. If the system does not pass, then a report is sent to the user and/or a remediation script is initiated to repair the problem. After software is installed, if errors arise that were not previously detected, a feedback mechanism sends the errors to the expert system library so future errors are detected preemptively.