That would happen if your local network was experiencing a network connectivity issue to the outside world. Restarting Roomie or your iOS device will force it to try again if you’d like and if you believe the local network connectivity issue has been resolved.
I actually don’t experience any LAN or WAN problems because I am able to connect to Internet easily via my iOS device and I have already forced the update several times but it failed.
Perhaps you’re on the East Coast impacted by regional network outages there due to the hurricane. We’d recommend switching network types (WiFi->3G) or waiting for the issue to resolve.
We can see a large number of users completing transactions successfully for updates and our servers at Amazon were not impacted during the recent outages.