fksdlofioenvdfsdji, 
How did you "want to update && upgrade your server"?
How many kernels can your /boot partition hold? (What is the size of your /boot 
partition?)

Contents of "50unattended-upgrades" is misleading, as there is no
mention of the new configuration variable Unattended-Upgrade::Remove-
New-Unused-Dependencies which defaults to "true" in the file (in Ubuntu
16.04).

Replacing line
// Unattended-Upgrade::Remove-Unused-Dependencies "false";
by
Unattended-Upgrade::Remove-Unused-Dependencies "true";
may help you, if you don't mind that it removes all packages that 'sudo apt-get 
autoremove' would.

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https://bugs.launchpad.net/bugs/1357093

Title:
  Kernels not autoremoving, causing out of space error on LVM or
  Encrypted installation or on any installation, when /boot partition
  gets full

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