Systems and methods for updating operating system software are provided. In some aspects, an update for an operating system of a computing device is received, at a first time, at the computing device. A pre-reboot state of the computing device is stored at a second time. The pre-reboot state includes login information for logging into the computing device as a specified user of the computing device, the specified user of the computing device being logged into the computing device at the second time. The computing device is rebooted. Prior to or during rebooting of the computing device, the operating system of the computing device is updated according to the received update. After rebooting the computing device, user access is provided to the updated operating system according to the stored pre-reboot state of the computing device.