Hey Justin,
Are you using the AutomaticUpdater or are you using wyUpdate as a standalone updater. If you're using the AutomaticUpdater then wyUpdate will restart your app if something fails mid-update.
If you're using wyUpdate in standalone mode then wyUpdate will automatically restart your service (if you're updating from a service). Or if you're updating a regular old app then you can use the "-startonerr" and "-startonerra" commandline options to start an application on an update error.
Does that make sense?