I regularly update my Trusty 3.13 kernel on Updates Manager notifications. As I do I such case, I remove the n-2 kernel just before upgrading so that my system remains with 2 kernel releases once the upgrade is done.
On last upgrade from 3.13.0-87 to 3.13.0-88, Updates Manager asked for reboot as usual, but once logged back in with -88, Update Manager asked again to reboot. Please, why ?
From How does Ubuntu keep track of the “System restart required” flag in motd? You can see which packages requested the reboot:
I try to remove old kernels before I do the reboot. The removal of a kernel re-runs grub and triggers the reboot.