Public bug reported:

apt-get suggests to remove and, with autoremove command, actually
removes previous kernel referenced by /*.old links and breaks the
ability to boot with a previous kernel. Kernel referenced by /*.old may
not be autoremoved.

# apt-get upgrade
Reading package lists... Done
Building dependency tree       
Reading state information... Done
Calculating upgrade... Done
The following packages were automatically installed and are no longer required:
  linux-headers-3.13.0-88 linux-headers-3.13.0-88-generic
  linux-image-3.13.0-88-generic linux-image-extra-3.13.0-88-generic
Use 'apt-get autoremove' to remove them.
0 upgraded, 0 newly installed, 0 to remove and 0 not upgraded.
Press any key to continue...

# ls -l /*.old
lrwxrwxrwx 1 root root 33 Jun 10 11:57 /initrd.img.old -> 
boot/initrd.img-3.13.0-88-generic
lrwxrwxrwx 1 root root 30 Jun 10 11:57 /vmlinuz.old -> 
boot/vmlinuz-3.13.0-88-generic

# uname -a
Linux server 3.13.0-100-generic #147-Ubuntu SMP Tue Oct 18 16:49:53 UTC 2016 
i686 athlon i686 GNU/Linux

** Affects: apt (Ubuntu)
     Importance: Undecided
         Status: New

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https://bugs.launchpad.net/bugs/1637797

Title:
  kernel referred to by /*.old autoremoved

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