APT should keep those kernels in recent versions:

# Mark as not-for-autoremoval those kernel packages that are:
#  - the currently booted version
#  - the kernel version we've been called for
#  - the latest kernel version (as determined by debian version number)
#  - the second-latest kernel version

I'm not sure what 1.0 does. Maybe it needs a cherry-pick of the fix for
Debian bug 772732

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

Title:
  kernel referred to by /*.old autoremoved

Status in apt package in Ubuntu:
  New

Bug description:
  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
  --- 
  ApportVersion: 2.14.1-0ubuntu3.21
  Architecture: i386
  DistroRelease: Ubuntu 14.04
  InstallationDate: Installed on 2011-08-18 (1899 days ago)
  InstallationMedia: Kubuntu 11.04 "Natty Narwhal" - Release i386 (20110427)
  NonfreeKernelModules: nvidia
  Package: apt 1.0.1ubuntu2.15
  PackageArchitecture: i386
  ProcVersionSignature: Ubuntu 3.13.0-100.147-generic 3.13.11-ckt39
  Tags:  trusty
  Uname: Linux 3.13.0-100-generic i686
  UpgradeStatus: Upgraded to trusty on 2014-10-18 (743 days ago)
  UserGroups:
   
  _MarkForUpload: True

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