Hi again,
After an automatic update it's about to happen again (I got a low disk space 
warning for /boot) so I'll list details and see what happens.

/boot$ ls -a -h -l
total 208M
drwxr-xr-x  4 root root 1.0K Jun 29 10:52 .
drwxr-xr-x 24 root root 4.0K Jun 29 10:51 ..
-rw-r--r--  1 root root 213K May 15 13:48 config-4.15.0-51-generic
-rw-r--r--  1 root root 213K Jun  4 21:33 config-4.15.0-52-generic
-rw-r--r--  1 root root 213K Jun 24 10:39 config-4.15.0-54-generic
drwxr-xr-x  5 root root 1.0K Jun 29 10:53 grub
-rw-r--r--  1 root root  57M Jun 21 18:21 initrd.img-4.15.0-51-generic
-rw-r--r--  1 root root  57M Jun 29 10:52 initrd.img-4.15.0-52-generic
-rw-r--r--  1 root root  57M Jun 29 10:52 initrd.img-4.15.0-54-generic
drwx------  2 root root  12K May 10 11:01 lost+found
-rw-r--r--  1 root root 179K Jan 28  2016 memtest86+.bin
-rw-r--r--  1 root root 181K Jan 28  2016 memtest86+.elf
-rw-r--r--  1 root root 181K Jan 28  2016 memtest86+_multiboot.bin
-rw-------  1 root root 3.9M May 15 13:48 System.map-4.15.0-51-generic
-rw-------  1 root root 3.9M Jun  4 21:33 System.map-4.15.0-52-generic
-rw-------  1 root root 3.9M Jun 24 10:39 System.map-4.15.0-54-generic
-rw-------  1 root root 8.0M May 15 15:11 vmlinuz-4.15.0-51-generic
-rw-------  1 root root 8.0M Jun  4 21:39 vmlinuz-4.15.0-52-generic
-rw-------  1 root root 8.0M Jun 24 11:21 vmlinuz-4.15.0-54-generic

Free space is listed as 7.1MB

Results of sudo apt autoremove
Reading package lists... Done
Building dependency tree       
Reading state information... Done
The following packages will be REMOVED
  linux-headers-4.15.0-51 linux-headers-4.15.0-51-generic
  linux-image-4.15.0-51-generic linux-modules-4.15.0-51-generic
  linux-modules-extra-4.15.0-51-generic
0 to upgrade, 0 to newly install, 5 to remove and 7 not to upgrade.
After this operation, 334 MB disk space will be freed.
Do you want to continue? [Y/n] y
(Reading database ... 233764 files and directories currently installed.)
Removing linux-headers-4.15.0-51-generic (4.15.0-51.55) ...
Removing linux-headers-4.15.0-51 (4.15.0-51.55) ...
Removing linux-modules-extra-4.15.0-51-generic (4.15.0-51.55) ...
Removing linux-image-4.15.0-51-generic (4.15.0-51.55) ...
/etc/kernel/postrm.d/initramfs-tools:
update-initramfs: Deleting /boot/initrd.img-4.15.0-51-generic
/etc/kernel/postrm.d/zz-update-grub:
Sourcing file `/etc/default/grub'
Generating grub configuration file ...
Found linux image: /boot/vmlinuz-4.15.0-54-generic
Found initrd image: /boot/initrd.img-4.15.0-54-generic
Found linux image: /boot/vmlinuz-4.15.0-52-generic
Found initrd image: /boot/initrd.img-4.15.0-52-generic
Found memtest86+ image: /memtest86+.elf
Found memtest86+ image: /memtest86+.bin
done
Removing linux-modules-4.15.0-51-generic (4.15.0-51.55) ...

Not all of this 334MB has been cleared from /boot
Here is another file listing:

total 139M
drwxr-xr-x  4 root root 1.0K Jun 29 11:07 .
drwxr-xr-x 24 root root 4.0K Jun 29 10:51 ..
-rw-r--r--  1 root root 213K Jun  4 21:33 config-4.15.0-52-generic
-rw-r--r--  1 root root 213K Jun 24 10:39 config-4.15.0-54-generic
drwxr-xr-x  5 root root 1.0K Jun 29 11:07 grub
-rw-r--r--  1 root root  57M Jun 29 10:52 initrd.img-4.15.0-52-generic
-rw-r--r--  1 root root  57M Jun 29 10:52 initrd.img-4.15.0-54-generic
drwx------  2 root root  12K May 10 11:01 lost+found
-rw-r--r--  1 root root 179K Jan 28  2016 memtest86+.bin
-rw-r--r--  1 root root 181K Jan 28  2016 memtest86+.elf
-rw-r--r--  1 root root 181K Jan 28  2016 memtest86+_multiboot.bin
-rw-------  1 root root 3.9M Jun  4 21:33 System.map-4.15.0-52-generic
-rw-------  1 root root 3.9M Jun 24 10:39 System.map-4.15.0-54-generic
-rw-------  1 root root 8.0M Jun  4 21:39 vmlinuz-4.15.0-52-generic
-rw-------  1 root root 8.0M Jun 24 11:21 vmlinuz-4.15.0-54-generic

There is now 79.5MB in /boot  Is this enough.  I'm suggesting not since
this keeps recurring.  Autoremove may indeed be working fine, but it
seems to me that the default installer has set the /boot partition size
value inappropriately low.  Am I right?

I suspect that when I posted the OP, that autoremove merely couldn't
remove enough space for a bulky update, rather than 'didn't work' as I
wrote.

Thanks

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https://bugs.launchpad.net/bugs/1833556

Title:
  Default, encrypted install runs out of /boot space after 2 months

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