In trying to troubleshoot this on a production server I noticed the issue is 
actually with linux-image-extra-4.4.0-87-generic. In the apt-auto-remove post 
install script, the linux-image-extra-4.4.0-87-generic creates a segfault.
<code>
$ sudo apt-get install linux-image-extra-4.4.0-81-generic --reinstall
Reading package lists... Done
Building dependency tree       
Reading state information... Done
The following additional packages will be installed:
  linux-image-4.4.0-81-generic
Suggested packages:
  fdutils linux-doc-4.4.0 | linux-source-4.4.0 linux-tools 
linux-headers-4.4.0-81-generic
The following packages will be REMOVED:
  linux-image-extra-4.4.0-83-generic linux-image-extra-4.4.0-87-generic
The following NEW packages will be installed:
  linux-image-4.4.0-81-generic
0 upgraded, 1 newly installed, 1 reinstalled, 2 to remove and 0 not upgraded.
4 not fully installed or removed.
Need to get 57.8 MB of archives.
After this operation, 238 MB disk space will be freed.
Do you want to continue? [Y/n] y
Get:1 http://us.archive.ubuntu.com/ubuntu xenial-updates/main amd64 
linux-image-4.4.0-81-generic amd64 4.4.0-81.104 [21.9 MB]
Get:2 http://us.archive.ubuntu.com/ubuntu xenial-updates/main amd64 
linux-image-extra-4.4.0-81-generic amd64 4.4.0-81.104 [35.9 MB]
Fetched 57.8 MB in 2s (21.8 MB/s)                             
(Reading database ... 41132 files and directories currently installed.)
Removing linux-image-extra-4.4.0-83-generic (4.4.0-83.106) ...
depmod: FATAL: could not load /boot/System.map-4.4.0-83-generic: No such file 
or directory
run-parts: executing /etc/kernel/postinst.d/apt-auto-removal 4.4.0-83-generic 
/boot/vmlinuz-4.4.0-83-generic
Segmentation fault (core dumped)
run-parts: /etc/kernel/postinst.d/apt-auto-removal exited with return code 139
dpkg: error processing package linux-image-extra-4.4.0-83-generic (--remove):
 subprocess installed post-removal script returned error exit status 1
Removing linux-image-extra-4.4.0-87-generic (4.4.0-87.110) ...
run-parts: executing /etc/kernel/postinst.d/apt-auto-removal 4.4.0-87-generic 
/boot/vmlinuz-4.4.0-87-generic
Segmentation fault (core dumped)
run-parts: /etc/kernel/postinst.d/apt-auto-removal exited with return code 139
dpkg: error processing package linux-image-extra-4.4.0-87-generic (--remove):
 subprocess installed post-removal script returned error exit status 1
Errors were encountered while processing:
 linux-image-extra-4.4.0-83-generic
 linux-image-extra-4.4.0-87-generic
E: Sub-process /usr/bin/dpkg returned an error code (1)
</code>

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https://bugs.launchpad.net/bugs/1706128

Title:
  package linux-image-4.4.0-87-generic (not installed) failed to
  install/upgrade: subprocess new pre-installation script returned error
  exit status 1

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