Systems and methods for remotely installing software on a computing system while the computing system is running on a first bootable image, so that the computing system is not removed from operation during the installation of a second bootable image. The method comprises constructing the second bootable image on a storage medium accessible to the computing system while the computing system is operating in a first operating environment in association with the first bootable image, customizing the second bootable image so that the computing system can operate in a second operating environment in association with the second bootable image, disassociating the computing system from the first bootable image, and associating the computing system with the second bootable image.