** Merge proposal linked:
   
https://code.launchpad.net/~athos-ribeiro/ubuntu/+source/openssh/+git/openssh/+merge/406318

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https://bugs.launchpad.net/bugs/1905285

Title:
  socket-activated sshd breaks on concurrent connections

Status in openssh package in Ubuntu:
  Fix Released
Status in openssh source package in Focal:
  In Progress
Status in openssh source package in Hirsute:
  New

Bug description:
  [Impact]

  Users of the systemd socket activated ssh service may experience a
  race condition that may lead an ssh instance to fail.

  The race condition happens when, for a running socket activated ssh
  service,

  an instance A is started, creating the RuntimeDirectory for the
  service; then

  an instance B is started, relying on the RuntimeDirectory created for
  instance A; then

  instance A halts, causing the RuntimeDirectory to be deleted.

  If, at this point, instance B has not chrooted into RuntimeDirectory
  yet, then instance B will fail.

  The proposed patch fixes the issue by preserving the RuntimeDirectory
  after an instance A of the socket activated ssh service halts.

  [Test Plan]

  1) Stop any running instances of ssh.
  `systemctl stop ssh`

  2) Start the socket activated ssh service.
  `systemctl start ssh.socket`

  3) Verify that no errors related to ssh were logged in /var/log/auth.log
  `cat /var/log/auth.log | grep 'sshd.*fatal.*chroot.*No such file or 
directory'`

  4) perform several ssh connections to the running server in a short time 
span. ssh-keyscan may help here.
  `ssh-keyscan localhost`

  5) Verify that errors related to ssh were logged in /var/log/auth.log
  `cat /var/log/auth.log | grep 'sshd.*fatal.*chroot.*No such file or 
directory'`

  6) Apply the proposed fix (make sure the socket activated service is
  restarted)

  7) repead step (4), then verify that no new entries were appended to
  the step (5) output

  [Where problems could occur]

  If the changes to the socket activated unit file are wrong, the socket
  activated service may fail to start after the package upgrade. In this
  case, we would need to instruct users to perform local changes to the
  unit file with possible additional fixes while a new version of the
  patch lands.

  [racb] There might be cases where users are inadvertently depending on
  the cleanup that will now be disabled - for example by a bug or
  misconfiguration that would result in /run filling up otherwise. By
  disabling systemd cleanup and relying solely on openssh for cleanup,
  such a bug or misconfiguration may be exposed and cause problems on
  such systems.

  [Other Info]

  This fix has been forwarded to Debian and accepted in
  https://salsa.debian.org/ssh-team/openssh/-/merge_requests/12

  [Original message]

  This is mostly the same issue as https://bugs.debian.org/cgi-
  bin/bugreport.cgi?bug=934663.

  With the default configuration of openssh-server and systemd, sshd
  will complain and crash when multiple connections are made and
  terminated in a quick succession, e.g. with `ssh-keyscan`. It results
  in the following errors in /var/log/auth.log:

  ```
  Nov 22 20:53:34 {host} sshd[14567]: Unable to negotiate with {client} port 
41460: no matching host key type found. Their offer: 
sk-ecdsa-sha2-nistp...@openssh.com [preauth]
  Nov 22 20:53:34 {host} sshd[14570]: fatal: chroot("/run/sshd"): No such file 
or directory [preauth]
  Nov 22 20:53:34 {host} sshd[14569]: fatal: chroot("/run/sshd"): No such file 
or directory [preauth]
  Nov 22 20:53:34 {host} sshd[14568]: fatal: chroot("/run/sshd"): No such file 
or directory [preauth]
  Nov 22 20:53:34 {host} sshd[14566]: fatal: chroot("/run/sshd"): No such file 
or directory [preauth]
  Nov 22 20:53:47 {host} sshd[14584]: Connection closed by {client} port 59312 
[preauth]
  Nov 22 20:53:47 {host} sshd[14586]: fatal: chroot("/run/sshd"): No such file 
or directory [preauth]
  Nov 22 20:53:48 {host} sshd[14585]: fatal: chroot("/run/sshd"): No such file 
or directory [preauth]
  ```

  as well as e.g. missing responses in ssh-keyscan:

  ```
  $ ssh-keyscan -vvv {host}
  debug2: fd 3 setting O_NONBLOCK
  debug3: conalloc: oname {host} kt 2
  debug2: fd 4 setting O_NONBLOCK
  debug3: conalloc: oname {host} kt 4
  debug2: fd 5 setting O_NONBLOCK
  debug3: conalloc: oname {host} kt 8
  debug2: fd 6 setting O_NONBLOCK
  debug3: conalloc: oname {host} kt 32
  debug2: fd 7 setting O_NONBLOCK
  debug3: conalloc: oname {host} kt 64
  debug1: match: OpenSSH_8.2p1 Ubuntu-4ubuntu0.1 pat OpenSSH* compat 0x04000000
  # {host}:22 SSH-2.0-OpenSSH_8.2p1 Ubuntu-4ubuntu0.1
  debug3: send packet: type 20
  debug1: SSH2_MSG_KEXINIT sent
  debug3: receive packet: type 20
  debug1: SSH2_MSG_KEXINIT received
  debug2: local client KEXINIT proposal
  debug2: KEX algorithms: 
curve25519-sha256,curve25519-sha...@libssh.org,ecdh-sha2-nistp256,ecdh-sha2-nistp384,ecdh-sha2-nistp521,diffie-hellman-group-exchange-sha256,diffie-hellman-group16-sha512,diffie-hellman-group18-sha512,diffie-hellman-group14-sha256
  debug2: host key algorithms: sk-ecdsa-sha2-nistp...@openssh.com
  debug2: ciphers ctos: 
chacha20-poly1...@openssh.com,aes128-ctr,aes192-ctr,aes256-ctr,aes128-...@openssh.com,aes256-...@openssh.com
  debug2: ciphers stoc: 
chacha20-poly1...@openssh.com,aes128-ctr,aes192-ctr,aes256-ctr,aes128-...@openssh.com,aes256-...@openssh.com
  debug2: MACs ctos: 
umac-64-...@openssh.com,umac-128-...@openssh.com,hmac-sha2-256-...@openssh.com,hmac-sha2-512-...@openssh.com,hmac-sha1-...@openssh.com,umac...@openssh.com,umac-...@openssh.com,hmac-sha2-256,hmac-sha2-512,hmac-sha1
  debug2: MACs stoc: 
umac-64-...@openssh.com,umac-128-...@openssh.com,hmac-sha2-256-...@openssh.com,hmac-sha2-512-...@openssh.com,hmac-sha1-...@openssh.com,umac...@openssh.com,umac-...@openssh.com,hmac-sha2-256,hmac-sha2-512,hmac-sha1
  debug2: compression ctos: none,z...@openssh.com
  debug2: compression stoc: none,z...@openssh.com
  debug2: languages ctos:
  debug2: languages stoc:
  debug2: first_kex_follows 0
  debug2: reserved 0
  debug2: peer server KEXINIT proposal
  debug2: KEX algorithms: 
curve25519-sha256,curve25519-sha...@libssh.org,ecdh-sha2-nistp256,ecdh-sha2-nistp384,ecdh-sha2-nistp521,diffie-hellman-group-exchange-sha256,diffie-hellman-group16-sha512,diffie-hellman-group18-sha512,diffie-hellman-group14-sha256,diffie-hellman-group14-sha1
  debug2: host key algorithms: 
rsa-sha2-512,rsa-sha2-256,ssh-rsa,ecdsa-sha2-nistp256,ssh-ed25519
  debug2: ciphers ctos: 
chacha20-poly1...@openssh.com,aes128-ctr,aes192-ctr,aes256-ctr,aes128-...@openssh.com,aes256-...@openssh.com
  debug2: ciphers stoc: 
chacha20-poly1...@openssh.com,aes128-ctr,aes192-ctr,aes256-ctr,aes128-...@openssh.com,aes256-...@openssh.com
  debug2: MACs ctos: 
umac-64-...@openssh.com,umac-128-...@openssh.com,hmac-sha2-256-...@openssh.com,hmac-sha2-512-...@openssh.com,hmac-sha1-...@openssh.com,umac...@openssh.com,umac-...@openssh.com,hmac-sha2-256,hmac-sha2-512,hmac-sha1
  debug2: MACs stoc: 
umac-64-...@openssh.com,umac-128-...@openssh.com,hmac-sha2-256-...@openssh.com,hmac-sha2-512-...@openssh.com,hmac-sha1-...@openssh.com,umac...@openssh.com,umac-...@openssh.com,hmac-sha2-256,hmac-sha2-512,hmac-sha1
  debug2: compression ctos: none,z...@openssh.com
  debug2: compression stoc: none,z...@openssh.com
  debug2: languages ctos:
  debug2: languages stoc:
  debug2: first_kex_follows 0
  debug2: reserved 0
  debug1: kex: algorithm: curve25519-sha256
  debug1: kex: host key algorithm: (no match)
  debug1: match: OpenSSH_8.2p1 Ubuntu-4ubuntu0.1 pat OpenSSH* compat 0x04000000
  # {host}:22 SSH-2.0-OpenSSH_8.2p1 Ubuntu-4ubuntu0.1
  debug3: send packet: type 20
  debug1: SSH2_MSG_KEXINIT sent
  debug1: match: OpenSSH_8.2p1 Ubuntu-4ubuntu0.1 pat OpenSSH* compat 0x04000000
  # {host}:22 SSH-2.0-OpenSSH_8.2p1 Ubuntu-4ubuntu0.1
  debug3: send packet: type 20
  debug1: SSH2_MSG_KEXINIT sent
  debug1: match: OpenSSH_8.2p1 Ubuntu-4ubuntu0.1 pat OpenSSH* compat 0x04000000
  # {host}:22 SSH-2.0-OpenSSH_8.2p1 Ubuntu-4ubuntu0.1
  debug3: send packet: type 20
  debug1: SSH2_MSG_KEXINIT sent
  debug1: match: OpenSSH_8.2p1 Ubuntu-4ubuntu0.1 pat OpenSSH* compat 0x04000000
  # {host}:22 SSH-2.0-OpenSSH_8.2p1 Ubuntu-4ubuntu0.1
  debug3: send packet: type 20
  debug1: SSH2_MSG_KEXINIT sent
  ```

  The error is most likely caused by a race condition on removing /run/sshd, 
which is easily reproducible by ssh-keyscan.
  I noticed that depeding on client, I'd sometimes miss all keys, sometimes get 
one, sometimes more.

  Modifying the following files (they should me marked as modified in the bug 
report) seems to solve the issue, at least temporarily:
  /usr/lib/systemd/system/ssh.service
  /usr/lib/systemd/system/ssh@.service
  In both cases, I added `RuntimeDirectoryPreserve=yes` to the `[Service]` 
section, after `RuntimeDirectory=sshd`.
  This is the same solution mentioned in the Debian bug, although their bug 
report doesn't mention which service files are affected.

  This doesn't seem to be a proper long-term solution though, as it seems apt 
doesn't respect configuration files in /usr (or they are unlisted somewhere),
  because after upgrading system just before filing this bug report, the files 
got overwritten and reverted to their original form.
  I only got asked about the /etc/ssh/sshd_config, which I have chosen to keep.

  ProblemType: Bug
  DistroRelease: Ubuntu 20.04
  Package: openssh-server 1:8.2p1-4ubuntu0.1 [modified: 
lib/systemd/system/ssh.service lib/systemd/system/ssh@.service]
  ProcVersionSignature: Ubuntu 5.4.0-54.60-generic 5.4.65
  Uname: Linux 5.4.0-54-generic x86_64
  ApportVersion: 2.20.11-0ubuntu27.12
  Architecture: amd64
  CasperMD5CheckResult: skip
  Date: Mon Nov 23 15:09:32 2020
  SourcePackage: openssh
  UpgradeStatus: No upgrade log present (probably fresh install)

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