Hello Dominik and thanks for this bug report. An umbrella bug report
doesn't really help here, especially given that there's no single "reset
config files on updates" policy in Ubuntu. Actually it's quite the
contrary: as a Debian derivative Ubuntu basically inherits [1] and in
particular [2].

Please file individual bug reports against the affected packages,
possibly providing steps to reproduce the problem. In the case of
openssh-server I can say that the overwrite shouldn't happen, as
ssh_config is handles via ucf [3]. But let's discuss this in a dedicated
bug, once opened. I'll just add that the newer versions of openssh-
server support dropping custom config snippets in
/etc/ssh/sshd_config.d/, for easier handling of custom configurations.

Thanks!

[1] https://www.debian.org/doc/debian-policy/ch-files.html#configuration-files
[2] https://www.debian.org/doc/debian-policy/ch-files.html#behavior
[3] http://manpages.ubuntu.com/manpages/focal/man1/ucf.1.html

** Changed in: openssh (Ubuntu)
       Status: New => Incomplete

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https://bugs.launchpad.net/bugs/1929854

Title:
  Vital and critical configuration files get overridden by system
  updates without warning

Status in grub2 package in Ubuntu:
  New
Status in libx11 package in Ubuntu:
  New
Status in openssh package in Ubuntu:
  Incomplete

Bug description:
  • In my /usr/share/X11/locale/en_US.UTF-8/Compose I have about 10'000 lines 
of special compose keys defined.
  • In my /boot/grub/grub.cfg I have a very complicated special setup for my 
various boot configurations, and a 5-sec timout for my EFI-config.
  • My /etc/ssh/sshd_config contains a well-balanced configuration 

  All these files are regularly overridden WITHOUT EVEN A SINGLE WARNING
  or ASKING BACK by ubuntu system setups (discover).

  I set all of them to read-only by root and no-access for group and
  other users, but they still get overridden by every other system
  update.  I even have a shutdown process in place which should actually
  make sure that changes to these files are reverted by writing a backup
  copy over any newly installed override — unfortunately, everything I
  did to run either a custom shutdown process or a startup process with
  systemd turned out to not work and be a nightmare to make work.

  How somebody could be as bold as to override vital configuration files
  like this without even asking  for consent is one of the strange
  miracles in this world which I'll probably never understand.  However,
  if "ubuntu" is really what it translates to, it should take a little
  bit more care about pre-existing configurations on systems on which it
  is set up and running well — until one system update suddenly
  jeopardizes the functioning of the entire system.  I'm pretty sure
  these are not the only configuration files which are carelessly just
  overridden.  They're just the ones every other update breaks my system
  and inflinges on my the costs of hours of research until I find out
  that — of course — it was an overridden critical system configuration
  again.  The really mean thing is that you don't notice anything when
  you run the update … only next time you start your system and of
  course are not aware anymore that you did a system update, the new
  (absolutely wrong and/or insufficent) settings are in place and shoot
  you in the leg.

  Take an example from gentoo's etc-update feature which lets you merge
  new configuration files with pre-existing ones using a diff3-update.
  I went away from gentoo for other reasons, but I always praised that
  feature.

  Please make sure immediately that critical configuration files do not
  get overridden if they are non-writable by root, and then gradually
  introduce a system that merges changes to configuration files with the
  current situation on the target system.  Or at least present the
  configs that would be changed in a particular directory, so that
  anybody who is interested in preserving local settings could merge
  them in a suitable way.

  Thanks

  ProblemType: Bug
  DistroRelease: Ubuntu 20.10
  Package: xorg 1:7.7+19ubuntu15
  ProcVersionSignature: Ubuntu 5.8.0-53.60-generic 5.8.18
  Uname: Linux 5.8.0-53-generic x86_64
  ApportVersion: 2.20.11-0ubuntu50.7
  Architecture: amd64
  BootLog: Error: [Errno 13] Permission denied: '/var/log/boot.log'
  CasperMD5CheckResult: skip
  CompositorRunning: None
  CurrentDesktop: KDE
  Date: Thu May 27 18:48:15 2021
  DistUpgraded: Fresh install
  DistroCodename: groovy
  DistroVariant: ubuntu
  ExtraDebuggingInterest: Yes
  GraphicsCard:
   NVIDIA Corporation TU117GLM [Quadro T1000 Mobile] [10de:1fb9] (rev a1) 
(prog-if 00 [VGA controller])
     Subsystem: Lenovo TU117GLM [Quadro T1000 Mobile] [17aa:2297]
  InstallationDate: Installed on 2021-01-15 (132 days ago)
  InstallationMedia: Kubuntu 20.10 "Groovy Gorilla" - Release amd64 (20201022)
  MachineType: LENOVO 20QQS0KL13
  ProcKernelCmdLine: BOOT_IMAGE=/@/boot/vmlinuz-5.8.0-53-generic 
root=UUID=35cef147-e021-4bdd-b8db-31a3192c8a6a ro rootflags=subvol=@ quiet 
splash vt.handoff=7
  SourcePackage: xorg
  Symptom: display
  UpgradeStatus: No upgrade log present (probably fresh install)
  dmi.bios.date: 06/04/2020
  dmi.bios.release: 1.23
  dmi.bios.vendor: LENOVO
  dmi.bios.version: N2NET38W (1.23 )
  dmi.board.asset.tag: Not Available
  dmi.board.name: 20QQS0KL13
  dmi.board.vendor: LENOVO
  dmi.board.version: SDK0J40697 WIN
  dmi.chassis.asset.tag: ZF211710
  dmi.chassis.type: 10
  dmi.chassis.vendor: LENOVO
  dmi.chassis.version: None
  dmi.ec.firmware.release: 1.14
  dmi.modalias: 
dmi:bvnLENOVO:bvrN2NET38W(1.23):bd06/04/2020:br1.23:efr1.14:svnLENOVO:pn20QQS0KL13:pvrThinkPadP53:rvnLENOVO:rn20QQS0KL13:rvrSDK0J40697WIN:cvnLENOVO:ct10:cvrNone:
  dmi.product.family: ThinkPad P53
  dmi.product.name: 20QQS0KL13
  dmi.product.sku: LENOVO_MT_20QQ_BU_Think_FM_ThinkPad P53
  dmi.product.version: ThinkPad P53
  dmi.sys.vendor: LENOVO
  version.compiz: compiz N/A
  version.libdrm2: libdrm2 2.4.102-1ubuntu1
  version.libgl1-mesa-dri: libgl1-mesa-dri 20.2.6-0ubuntu0.20.10.1
  version.libgl1-mesa-glx: libgl1-mesa-glx N/A
  version.xserver-xorg-core: xserver-xorg-core 2:1.20.9-2ubuntu1.3
  version.xserver-xorg-input-evdev: xserver-xorg-input-evdev N/A
  version.xserver-xorg-video-ati: xserver-xorg-video-ati 1:19.1.0-1ubuntu1
  version.xserver-xorg-video-intel: xserver-xorg-video-intel 
2:2.99.917+git20200714-1
  version.xserver-xorg-video-nouveau: xserver-xorg-video-nouveau 1:1.0.16-1

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