A method and system for implementing a live operating system upgrade of a computer system. The method includes generating a first copy of a previous operating system environment of the computer system. The computer system is then booted to a subsequent operating system environment. A second copy of the previous operating system environment at the time of the booting is then generated. Additionally, a third copy of the subsequent operating system environment, at the time of the booting is generated. The copies function by ensuring the subsequent operating system environment is synchronized with the previous operating system environment by comparing the first copy, the second copy, and the third copy to detect any intervening changes and allow decisions to be made regarding such changes.