I was able to repair it by forcing the upgrade:
rpm -Uvh --force openssl-*
rpm -Uvh --force libopenssl0_9_8-0.9.8j-0.44.1.x86_64.rpm
rpm -Uvh --force openssh-5.1p1-41.55.1.x86_64.rpm
The SSL/SSH components were working again, but it still was letting me update it. Post Installation Scripts failed.
After all, we decided to just re-deploy a new appliance, not to loose even more time.