Patching, upgrading, and maintaining operating system software is a growing management complexity problem that can result in unacceptable system downtime. We introduce AutoPod, a system that enables unscheduled operating system updates while preserving application service availability. AutoPod provides a group of processes and associated users with an isolated machine-independent virtualized environment that is decoupled from the underlying operating system instance. This virtualized environment is integrated with a novel checkpoint-restart mechanism which allows processes to be suspended, resumed, and migrated across operating system kernel versions with different security and maintenance patches. AutoPod incorporates a system status service to determine when operating system patches need to be applied to the current host, then automatically migrates application services to another host to preserve their availability while the current host is updated and rebooted.