Might I suggest a bug be created for the behavior I saw regarding
removing other kernels.

Specifically, I upgraded to a kernel and the upgrade largely failed,
even thought it was allowed to proceed and was not backed out.
Automatically backing out of a failing upgrade might be yet another
feature request - qualitatively evaluating (programatically) an upgrade
would be an interesting, large, and valuable project.  This would add
quite a bit of value to Linux users.

What I'm focused on, however is the fact that apt told me to remove
older kernels as they were no longer needed, even though the current
system didn't even have a functional network after the upgrade.  Someone
not paying attention might follow these instructions obediently removing
the old kernels.  Unless I'm mistaken, that would leave zero
alternatives to boot to a functioning (i.e.- with networking) system.
This little note from apt would escalate the severity of the failed
upgrade exponentially.

What I'm not sure about is if the message was asking me to remove all
older kernels or just the oldest of them.  If it was suggesting I remove
some but not all older kernels, this point would be moot.

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You received this bug notification because you are a member of Kernel
Packages, which is subscribed to linux in Ubuntu.
https://bugs.launchpad.net/bugs/1672224

Title:
  Upgrade to kernel version 4.4.0-66 of Ubuntu 16.04 LTS caused major
  chaos/failures

Status in linux package in Ubuntu:
  Confirmed
Status in linux source package in Xenial:
  Confirmed

Bug description:
  The most obvious issue upon logging in was that there were no network 
interfaces save the loopback.
  A review of the logs suggested there were many major problems with the 
upgrade.

  Interestingly, the system suggested that I delete all other versions
  of the kernel immediately after this failed upgrade.  This would have
  rendered the system nearly unusable.

  This is not the user experience I was thinking of when I chose an LTS
  version.

  ProblemType: Bug
  DistroRelease: Ubuntu 16.04
  Package: linux-image-4.4.0-66-generic 4.4.0-66.87
  ProcVersionSignature: Ubuntu 4.4.0-63.84-generic 4.4.44
  Uname: Linux 4.4.0-63-generic x86_64
  NonfreeKernelModules: nvidia_uvm nvidia_drm nvidia_modeset nvidia
  ApportVersion: 2.20.1-0ubuntu2.5
  Architecture: amd64
  AudioDevicesInUse:
   USER        PID ACCESS COMMAND
   /dev/snd/controlC1:  doug       2348 F.... pulseaudio
   /dev/snd/controlC2:  doug       2348 F.... pulseaudio
   /dev/snd/controlC0:  doug       2348 F.... pulseaudio
  CurrentDesktop: Unity
  Date: Sun Mar 12 15:23:41 2017
  EcryptfsInUse: Yes
  HibernationDevice: RESUME=UUID=caabec9a-7ba2-451a-91a5-af1bef3bfc38
  InstallationDate: Installed on 2017-01-20 (51 days ago)
  InstallationMedia: Ubuntu 16.04 LTS "Xenial Xerus" - Release amd64 
(20160420.1)
  IwConfig:
   lo        no wireless extensions.

   enp6s0    no wireless extensions.
  MachineType: System manufacturer System Product Name
  ProcEnviron:
   LANGUAGE=en_US
   PATH=(custom, no user)
   XDG_RUNTIME_DIR=<set>
   LANG=en_US.UTF-8
   SHELL=/bin/bash
  ProcFB: 0 VESA VGA
  ProcKernelCmdLine: BOOT_IMAGE=/vmlinuz-4.4.0-63-generic 
root=UUID=ecd4d068-85e7-40c9-8483-d2dbfaadc20b ro rootflags=subvol=@ quiet 
splash vt.handoff=7
  RelatedPackageVersions:
   linux-restricted-modules-4.4.0-63-generic N/A
   linux-backports-modules-4.4.0-63-generic  N/A
   linux-firmware                            1.157.8
  RfKill:

  SourcePackage: linux
  UpgradeStatus: No upgrade log present (probably fresh install)
  dmi.bios.date: 12/10/2013
  dmi.bios.vendor: American Megatrends Inc.
  dmi.bios.version: 0908
  dmi.board.asset.tag: To be filled by O.E.M.
  dmi.board.name: P8Z77-V LE PLUS
  dmi.board.vendor: ASUSTeK COMPUTER INC.
  dmi.board.version: Rev X.0x
  dmi.chassis.asset.tag: Asset-1234567890
  dmi.chassis.type: 3
  dmi.chassis.vendor: Chassis Manufacture
  dmi.chassis.version: Chassis Version
  dmi.modalias: 
dmi:bvnAmericanMegatrendsInc.:bvr0908:bd12/10/2013:svnSystemmanufacturer:pnSystemProductName:pvrSystemVersion:rvnASUSTeKCOMPUTERINC.:rnP8Z77-VLEPLUS:rvrRevX.0x:cvnChassisManufacture:ct3:cvrChassisVersion:
  dmi.product.name: System Product Name
  dmi.product.version: System Version
  dmi.sys.vendor: System manufacturer

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