A system and method for rebooting an operating system into a recovery environment. A computing system is configured to reboot an operating system into a recovery environment which mimics the environment of an installed operating system. Subsequent to initiating the reboot, the system performs a discovery operation to identify operating systems which are installed on the system. Upon identifying a type and/or version of an operating system which is installed, processes corresponding to an identified operating system are initiated to determine configuration information of the operating system. Subsequently, the determined configuration information is used to establish an environment for the recovery environment which mimics that of the installed operating system. Discovery procedures may include discovering physical disks coupled to the system, identifying logical volumes on each of the disks, and examining each of the logical volumes for installed operating systems. Ordinary boot of the system, and reboot of the system, may be accomplished via different devices. Reboot may be accomplished via portable media such as CD-ROM.