[Bug 1873528] Re: sshd overrides from /etc/ssh/sshd_config.d/*conf apply in reverse lexographic order

[Dimitri John Ledkov]

I wonder, if i can try doing that with core22

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Title:
  sshd overrides from /etc/ssh/sshd_config.d/*conf apply in reverse
  lexographic order

Status in openssh package in Ubuntu:
  Invalid

Bug description:
  I am looking at the addition of 'Include /etc/ssh/sshd_config.d/*conf'
  for use in Ubuntu cloud images.  I wanted to add a config file and see
  if I had done things correctly.  I assumed that the files were sourced
  lexographically (based on use of glob() in readconf.h) so that I could
  document how users could override our tuning.  But it appears from
  'sshd -T' output and observed behavior that the first file in
  /etc/sshd_config.d/ to define a parameter wins.  I see in 'sshd -ddd'
  output that they are parsed lexographically but it seems that their
  settings apply in reverse (or whichever comes first) if that makes
  sense.  I'd like to understand if this is correct behavior and get it
  documented.

  Steps to reproduce on focal with openssh-server 1:8.2p1-4:

  1. Create the following files in /etc/ssh/sshd_config.d/ with the content shown below:
  40-cloudimg-settings.conf:
    ClientAliveInterval 110
    PasswordAuthentication yes
    PermitRootLogin no

  50-cloudimg-settings.conf:
    ClientAliveInterval 120
    PermitRootLogin yes

  60-cloudimg-settings.conf:
    ClientAliveInterval 180

  2. Check what sshd thinks the values will be with 'sshd -T|grep -i clientaliveinterval' and 'sshd -T|grep permitrootlogin'
  clientaliveinterval 110
  permitrootlogin no

  (The tuning I cared about was ClientAliveInterval for my work but
  PermitRootLogin is easier to demonstrate)

  3. Run '/usr/sbin/sshd -ddd' to check debug output for config file parsing behavior:
  debug2: load_server_config: filename /etc/ssh/sshd_config
  debug2: load_server_config: done config len = 296
  debug2: parse_server_config_depth: config /etc/ssh/sshd_config len 296
  debug2: /etc/ssh/sshd_config line 13: new include /etc/ssh/sshd_config.d/*.conf
  debug2: /etc/ssh/sshd_config line 13: including /etc/ssh/sshd_config.d/40-cloudimg-settings.conf
  debug2: load_server_config: filename /etc/ssh/sshd_config.d/40-cloudimg-settings.conf
  debug2: load_server_config: done config len = 71
  debug2: parse_server_config_depth: config /etc/ssh/sshd_config.d/40-cloudimg-settings.conf len 71
  debug3: /etc/ssh/sshd_config.d/40-cloudimg-settings.conf:1 setting ClientAliveInterval 110
  debug3: /etc/ssh/sshd_config.d/40-cloudimg-settings.conf:2 setting PasswordAuthentication yes
  debug3: /etc/ssh/sshd_config.d/40-cloudimg-settings.conf:3 setting PermitRootLogin no
  debug2: /etc/ssh/sshd_config line 13: including /etc/ssh/sshd_config.d/50-cloudimg-settings.conf
  debug2: load_server_config: filename /etc/ssh/sshd_config.d/50-cloudimg-settings.conf
  debug2: load_server_config: done config len = 46
  debug2: parse_server_config_depth: config /etc/ssh/sshd_config.d/50-cloudimg-settings.conf len 46
  debug3: /etc/ssh/sshd_config.d/50-cloudimg-settings.conf:1 setting ClientAliveInterval 120
  debug3: /etc/ssh/sshd_config.d/50-cloudimg-settings.conf:2 setting PermitRootLogin yes
  debug2: /etc/ssh/sshd_config line 13: including /etc/ssh/sshd_config.d/60-cloudimg-settings.conf
  debug2: load_server_config: filename /etc/ssh/sshd_config.d/60-cloudimg-settings.conf
  debug2: load_server_config: done config len = 25
  debug2: parse_server_config_depth: config /etc/ssh/sshd_config.d/60-cloudimg-settings.conf len 25
  debug3: /etc/ssh/sshd_config.d/60-cloudimg-settings.conf:1 setting ClientAliveInterval 180

  4. Set a root password and unlock the account.

  5. Attempt to ssh as root to the instance with a password.

  Observation:
   * Root password login is denied if PermitRootLogin is 'no' in 40-foo.conf and 'yes' in 50-foo.conf
   * Root password login is allowed if PermitRootLogin is 'yes' in 40-foo.conf and 'no' in 50-foo.conf

  It appears in 'sshd -ddd' output that files are parsed in lexographic
  order (40-foo.conf before 50-foo.conf) but the behavior observed
  indicates that the value set in 40-foo.conf overrides 50-foo.conf
  which is counter to expectations.

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