Brian,
This weekend we had updates for libssl and a libssl regression. Both required a 
reboot and no second reboot. In other words worked as expected. 

Perhaps the bug only occurs for kernel updates. I have had this happen a few 
times in the past. So the next time it happens I will not run autoremove 
manually, to see what happens.
What files and logs can I provide at that time that will help?

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https://bugs.launchpad.net/bugs/1626345

Title:
  After rebooting for updates, reboot is still required.

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