Public bug reported:

I report this, because the problem has occurred several times during
recent upgrades:

A new kernel was installed during the upgrade, but the accompanying
kernel modules were not. As a consequence, the twofish modules were
missing, and encrypted volumes did not mount anymore. This resulted in
the error messages:

[  366.866643] device-mapper: table: 253:0: crypt: unknown target type          
[  366.867506] device-mapper: ioctl: error adding target to table 

lsmod and /proc/crypto revealed, that the twofish modules were not
loaded. Off course they were not, because
/lib/modules/4.10.0-37-generic/ did not exist. Apparently, linux-image-
extra-4.10.0-37-generic had not been installed alongside linux-
image-4.10.0-37-generic during the most recent upgrade. After manually
installing linux-image-extra, the encrypted volume mounted without
problems.

The package linux-image-extra should always be installed automatically
with a new kernel, if it was installed for the old kernel, to avoid this
and similar problems.

ProblemType: Bug
DistroRelease: Ubuntu 16.04
Package: update-manager 1:16.04.10
ProcVersionSignature: Ubuntu 4.10.0-37.41-generic 4.10.17
Uname: Linux 4.10.0-37-generic x86_64
NonfreeKernelModules: nvidia_drm nvidia_modeset nvidia
ApportVersion: 2.20.1-0ubuntu2.10
Architecture: amd64
CurrentDesktop: GNOME
Date: Wed Oct 25 10:35:36 2017
GsettingsChanges: b'com.ubuntu.update-manager' b'first-run' b'false'
InstallationDate: Installed on 2015-11-05 (719 days ago)
InstallationMedia: Ubuntu 14.04.3 LTS "Trusty Tahr" - Beta amd64 (20150805)
PackageArchitecture: all
SourcePackage: update-manager
UpgradeStatus: No upgrade log present (probably fresh install)

** Affects: update-manager (Ubuntu)
     Importance: Undecided
         Status: New


** Tags: amd64 apport-bug package-from-proposed third-party-packages xenial

** Attachment added: "dmesg.txt"
   https://bugs.launchpad.net/bugs/1727247/+attachment/4993836/+files/dmesg.txt

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https://bugs.launchpad.net/bugs/1727247

Title:
  Upgrade fails to automattically install modules with a new kernel

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