Authentication failures when using paramiko with an ssh-rsa-cert-v01@openssh.com public certificate

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I am working with an internal system that when asking for SSH keys, it returns three files:

  • id_rsa (presumably the private key)
  • id_rsa.pub (presumably the public key)
  • id_rsa-cert (A public key certificate?)

The -cert file begins with ssh-rsa-cert-v01@openssh.com which leads me to believe it is indeed the above linked public key although most sources speak of the -cert.pub extension.

If I connect to the machine using the SSH agent, it seems that everything's in working order, and the -cert file is recognized as "type 4":


OpenSSH_8.2p1 Ubuntu-4ubuntu0.4, OpenSSL 1.1.1f  31 Mar 2020
debug1: Reading configuration data /etc/ssh/ssh_config
debug1: /etc/ssh/ssh_config line 19: include /etc/ssh/ssh_config.d/*.conf matched no files
debug1: /etc/ssh/ssh_config line 21: Applying options for *
debug2: resolve_canonicalize: hostname 10.176.34.90 is address
debug2: ssh_connect_direct
debug1: Connecting to 10.176.34.90 [10.176.34.90] port 22.
debug1: Connection established.
debug1: identity file /tmp/id_rsa type 0
debug1: identity file /tmp/id_rsa-cert type 4
debug1: Local version string SSH-2.0-OpenSSH_8.2p1 Ubuntu-4ubuntu0.4
debug1: Remote protocol version 2.0, remote software version OpenSSH_7.4
debug1: match: OpenSSH_7.4 pat OpenSSH_7.0*,OpenSSH_7.1*,OpenSSH_7.2*,OpenSSH_7.3*,OpenSSH_7.4*,OpenSSH_7.5*,OpenSSH_7.6*,OpenSSH_7.7* compat 0x04000002
debug2: fd 3 setting O_NONBLOCK
debug1: Authenticating to 10.176.34.90:22 as 'ec2-user'
debug1: SSH2_MSG_KEXINIT sent
debug1: SSH2_MSG_KEXINIT received
debug2: local client KEXINIT proposal
debug2: KEX algorithms: curve25519-sha256,curve25519-sha256@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,ext-info-c
debug2: host key algorithms: ecdsa-sha2-nistp256-cert-v01@openssh.com,ecdsa-sha2-nistp384-cert-v01@openssh.com,ecdsa-sha2-nistp521-cert-v01@openssh.com,ecdsa-sha2-nistp256,ecdsa-sha2-nistp384,ecdsa-sha2-nistp521,sk-ecdsa-sha2-nistp256-cert-v01@openssh.com,ssh-ed25519-cert-v01@openssh.com,sk-ssh-ed25519-cert-v01@openssh.com,rsa-sha2-512-cert-v01@openssh.com,rsa-sha2-256-cert-v01@openssh.com,ssh-rsa-cert-v01@openssh.com,sk-ecdsa-sha2-nistp256@openssh.com,ssh-ed25519,sk-ssh-ed25519@openssh.com,rsa-sha2-512,rsa-sha2-256,ssh-rsa
debug2: ciphers ctos: chacha20-poly1305@openssh.com,aes128-ctr,aes192-ctr,aes256-ctr,aes128-gcm@openssh.com,aes256-gcm@openssh.com
debug2: ciphers stoc: chacha20-poly1305@openssh.com,aes128-ctr,aes192-ctr,aes256-ctr,aes128-gcm@openssh.com,aes256-gcm@openssh.com
debug2: MACs ctos: umac-64-etm@openssh.com,umac-128-etm@openssh.com,hmac-sha2-256-etm@openssh.com,hmac-sha2-512-etm@openssh.com,hmac-sha1-etm@openssh.com,umac-64@openssh.com,umac-128@openssh.com,hmac-sha2-256,hmac-sha2-512,hmac-sha1
debug2: MACs stoc: umac-64-etm@openssh.com,umac-128-etm@openssh.com,hmac-sha2-256-etm@openssh.com,hmac-sha2-512-etm@openssh.com,hmac-sha1-etm@openssh.com,umac-64@openssh.com,umac-128@openssh.com,hmac-sha2-256,hmac-sha2-512,hmac-sha1
debug2: compression ctos: none,zlib@openssh.com,zlib
debug2: compression stoc: none,zlib@openssh.com,zlib
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-sha256@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-group-exchange-sha1,diffie-hellman-group14-sha256,diffie-hellman-group14-sha1,diffie-hellman-group1-sha1
debug2: host key algorithms: ssh-rsa,rsa-sha2-512,rsa-sha2-256,ecdsa-sha2-nistp256,ssh-ed25519
debug2: ciphers ctos: chacha20-poly1305@openssh.com,aes128-ctr,aes192-ctr,aes256-ctr,aes128-gcm@openssh.com,aes256-gcm@openssh.com,aes128-cbc,aes192-cbc,aes256-cbc,blowfish-cbc,cast128-cbc,3des-cbc
debug2: ciphers stoc: chacha20-poly1305@openssh.com,aes128-ctr,aes192-ctr,aes256-ctr,aes128-gcm@openssh.com,aes256-gcm@openssh.com,aes128-cbc,aes192-cbc,aes256-cbc,blowfish-cbc,cast128-cbc,3des-cbc
debug2: MACs ctos: umac-64-etm@openssh.com,umac-128-etm@openssh.com,hmac-sha2-256-etm@openssh.com,hmac-sha2-512-etm@openssh.com,hmac-sha1-etm@openssh.com,umac-64@openssh.com,umac-128@openssh.com,hmac-sha2-256,hmac-sha2-512,hmac-sha1
debug2: MACs stoc: umac-64-etm@openssh.com,umac-128-etm@openssh.com,hmac-sha2-256-etm@openssh.com,hmac-sha2-512-etm@openssh.com,hmac-sha1-etm@openssh.com,umac-64@openssh.com,umac-128@openssh.com,hmac-sha2-256,hmac-sha2-512,hmac-sha1
debug2: compression ctos: none,zlib@openssh.com
debug2: compression stoc: none,zlib@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: ecdsa-sha2-nistp256
debug1: kex: server->client cipher: chacha20-poly1305@openssh.com MAC: <implicit> compression: none
debug1: kex: client->server cipher: chacha20-poly1305@openssh.com MAC: <implicit> compression: none
debug1: expecting SSH2_MSG_KEX_ECDH_REPLY
debug1: Server host key: ecdsa-sha2-nistp256 SHA256:dcU1jNy+H6haaVGW/O3KKyeQljaFII4B8uztw//VxLM
debug1: Host '10.176.34.90' is known and matches the ECDSA host key.
debug1: Found key in /home/wonderb0lt/.ssh/known_hosts:2
debug2: set_newkeys: mode 1
debug1: rekey out after 134217728 blocks
debug1: SSH2_MSG_NEWKEYS sent
debug1: expecting SSH2_MSG_NEWKEYS
debug1: SSH2_MSG_NEWKEYS received
debug2: set_newkeys: mode 0
debug1: rekey in after 134217728 blocks
debug1: Will attempt key: /tmp/id_rsa RSA SHA256:kmgmx/E7PzCEHvzSPIooMKpEHqmmCDMoRLMAF3JRvug explicit agent
debug1: Will attempt key: /tmp/id_rsa RSA-CERT SHA256:kmgmx/E7PzCEHvzSPIooMKpEHqmmCDMoRLMAF3JRvug explicit
debug2: pubkey_prepare: done
debug1: SSH2_MSG_EXT_INFO received
debug1: kex_input_ext_info: server-sig-algs=<rsa-sha2-256,rsa-sha2-512>
debug2: service_accept: ssh-userauth
debug1: SSH2_MSG_SERVICE_ACCEPT received
debug1: Authentications that can continue: publickey
debug1: Next authentication method: publickey
debug1: Offering public key: /tmp/id_rsa RSA SHA256:kmgmx/E7PzCEHvzSPIooMKpEHqmmCDMoRLMAF3JRvug explicit agent
debug2: we sent a publickey packet, wait for reply
debug1: Authentications that can continue: publickey
debug1: Offering public key: /tmp/id_rsa RSA-CERT SHA256:kmgmx/E7PzCEHvzSPIooMKpEHqmmCDMoRLMAF3JRvug explicit
debug2: we sent a publickey packet, wait for reply
debug1: Server accepts key: /tmp/id_rsa RSA-CERT SHA256:kmgmx/E7PzCEHvzSPIooMKpEHqmmCDMoRLMAF3JRvug explicit
debug2: sign_and_send_pubkey: using private key "/tmp/id_rsa" for certificate
debug1: Authentication succeeded (publickey).

However, when I try to do a similar connection attempt in paramiko with the following code:

pkey = RSAKey.from_private_key_file('/tmp/kx/id_rsa')
pkey.load_certificate('/tmp/kx/id_rsa-cert')
c = SSHClient()
c.set_missing_host_key_policy(AutoAddPolicy())
c.connect(hostname='10.176.33.64', username='ec2-user', pkey=pkey, allow_agent=False, look_for_keys=False)
print(c.exec_command('ls -l'))

I am greeted with an authentication exception:

DEBUG:paramiko.transport:starting thread (client mode): 0x6f9d3a60
DEBUG:paramiko.transport:Local version/idstring: SSH-2.0-paramiko_2.9.2
DEBUG:paramiko.transport:Remote version/idstring: SSH-2.0-OpenSSH_7.4
INFO:paramiko.transport:Connected (version 2.0, client OpenSSH_7.4)
DEBUG:paramiko.transport:=== Key exchange possibilities ===
DEBUG:paramiko.transport:kex algos: curve25519-sha256, curve25519-sha256@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-group-exchange-sha1, diffie-hellman-group14-sha256, diffie-hellman-group14-sha1, diffie-hellman-group1-sha1
DEBUG:paramiko.transport:server key: ssh-rsa, rsa-sha2-512, rsa-sha2-256, ecdsa-sha2-nistp256, ssh-ed25519
DEBUG:paramiko.transport:client encrypt: chacha20-poly1305@openssh.com, aes128-ctr, aes192-ctr, aes256-ctr, aes128-gcm@openssh.com, aes256-gcm@openssh.com, aes128-cbc, aes192-cbc, aes256-cbc, blowfish-cbc, cast128-cbc, 3des-cbc
DEBUG:paramiko.transport:server encrypt: chacha20-poly1305@openssh.com, aes128-ctr, aes192-ctr, aes256-ctr, aes128-gcm@openssh.com, aes256-gcm@openssh.com, aes128-cbc, aes192-cbc, aes256-cbc, blowfish-cbc, cast128-cbc, 3des-cbc
DEBUG:paramiko.transport:client mac: umac-64-etm@openssh.com, umac-128-etm@openssh.com, hmac-sha2-256-etm@openssh.com, hmac-sha2-512-etm@openssh.com, hmac-sha1-etm@openssh.com, umac-64@openssh.com, umac-128@openssh.com, hmac-sha2-256, hmac-sha2-512, hmac-sha1
DEBUG:paramiko.transport:server mac: umac-64-etm@openssh.com, umac-128-etm@openssh.com, hmac-sha2-256-etm@openssh.com, hmac-sha2-512-etm@openssh.com, hmac-sha1-etm@openssh.com, umac-64@openssh.com, umac-128@openssh.com, hmac-sha2-256, hmac-sha2-512, hmac-sha1
DEBUG:paramiko.transport:client compress: none, zlib@openssh.com
DEBUG:paramiko.transport:server compress: none, zlib@openssh.com
DEBUG:paramiko.transport:client lang: <none>
DEBUG:paramiko.transport:server lang: <none>
DEBUG:paramiko.transport:kex follows: False
DEBUG:paramiko.transport:=== Key exchange agreements ===
DEBUG:paramiko.transport:Kex: curve25519-sha256@libssh.org
DEBUG:paramiko.transport:HostKey: ssh-ed25519
DEBUG:paramiko.transport:Cipher: aes128-ctr
DEBUG:paramiko.transport:MAC: hmac-sha2-256
DEBUG:paramiko.transport:Compression: none
DEBUG:paramiko.transport:=== End of kex handshake ===
DEBUG:paramiko.transport:kex engine KexCurve25519 specified hash_algo <built-in function openssl_sha256>
DEBUG:paramiko.transport:Switch to new keys ...
DEBUG:paramiko.transport:Got EXT_INFO: {'server-sig-algs': b'rsa-sha2-256,rsa-sha2-512'}
DEBUG:paramiko.transport:Adding ssh-ed25519 host key for 10.176.33.64: b'b0878c9bc616a0c5fa69ee252730bc17'
DEBUG:paramiko.transport:Trying SSH key b'00f98d495396b7cdad1fa25c87e3f694'
DEBUG:paramiko.transport:userauth is OK
DEBUG:paramiko.transport:Finalizing pubkey algorithm for key of type 'ssh-rsa-cert-v01@openssh.com'
DEBUG:paramiko.transport:Our pubkey algorithm list: ['rsa-sha2-512', 'rsa-sha2-256', 'ssh-rsa']
DEBUG:paramiko.transport:Server-side algorithm list: ['rsa-sha2-256', 'rsa-sha2-512']
DEBUG:paramiko.transport:Agreed upon 'rsa-sha2-512' pubkey algorithm
INFO:paramiko.transport:Authentication (publickey) failed.

I am out of ideas. I've tried to switch out the pkey parameter for key_filename both referring to the -cert file as well as the private key, and I've also renamed the id_rsa-cert file to id_rsa-cert.pub in my desperation, all to no avail.

That the connection per SSH client works leads me to believe I'm using Paramiko wrong somehow. I'm aware of the issue with Paramiko >=2.9.0 and the server-sig-algs, but I don't think that's the issue. If I exclude the algorithms as the note suggests, but that just leads to another exception that no algorithm could be agreed upon - I'm fairly certain our servers are built just to accept these specific key types.

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