Ten years ago, I had a Debian server completely wedge itself on an update. glibc was hosed, practically nothing would run, and I couldn't untangle the mess. Had it been unattended, downtime would have been even longer than the hours it took to rebuild the box from scratch.
This was not the first or last time such an event would occur, merely the most severe.
Updates break things. Anyone who claims otherwise is either incredibly lucky, or incredibly inexperienced.
For a highly-available mission-critical infrastructure in 2013, the failure plan is also to rebuild from scratch, because "failure" means redundant and backup systems have exploded. This is most likely to occur when you automatically roll out untested changes to your infrastructure.
In either case, you won't be sleeping tonight. Or possibly tomorrow night.
I'm not sure how good the Ubuntu LTS relases are, but Debian has always been great at both keeping a stable system up, and keeping the upgrade to new version as painless as possible.
[1] "upgrade" if using apt-get, "safe-upgrade" if using aptitude
So I had the effect right, but the commands mixed up :-)
Might as well set it automatically and stay protected <shrugs>