PPK failed to authenticate after encrypting

[Neil Alwin Hermosilla]

Hello Team,

I am just wondering if someone had encounter the same error using ansible-vault.
Issue started after I encrypted the ppk using ansible-vault. For everyone to have an idea what I did, I will post the steps I've taken.

ansible-vault create vault-master

ansible-vault encrypt .ppk/user.ppk --vault-password-file vault-master

ansible-vault encrypt .ppk/user.ppk --vault-password-file vault-masterkey
Encryption successful

chmod 0400 .ppk/user.ppk

ansible all -m ping -u root --private-key=.ppk/user.ppk --vault-password-file vault-masterkey -vvvv

After typing the last command above, the log seems to have an unusual output. Here is what the -verbose mode shows.

<---> ESTABLISH CONNECTION FOR USER: root
<---> REMOTE_MODULE ping
<---> EXEC ['ssh', '-C', '-tt', '-vvv', '-o', 'ControlMaster=auto', '-o', 'ControlPersist=60s', '-o', 'ControlPath=/root/.ansible/cp/ansible-ssh-%h-%p-%r', '-o', 'IdentityFile=.ppk/user.ppk', '-o', 'KbdInteractiveAuthentication=no', '-o', 'PreferredAuthentications=gssapi-with-mic,gssapi-keyex,hostbased,publickey', '-o', 'PasswordAuthentication=no', '-o', 'ConnectTimeout=10', '---', "/bin/sh -c 'mkdir -p $HOME/.ansible/tmp/ansible-tmp-1443340552.33-274338782155659 && echo $HOME/.ansible/tmp/ansible-tmp-1443340552.33-274338782155659'"]
<128.199.129.6> ESTABLISH CONNECTION FOR USER: root
<128.199.129.6> REMOTE_MODULE ping
<128.199.129.6> EXEC ['ssh', '-C', '-tt', '-vvv', '-o', 'ControlMaster=auto', '-o', 'ControlPersist=60s', '-o', 'ControlPath=/root/.ansible/cp/ansible-ssh-%h-%p-%r', '-o', 'IdentityFile=.ppk/user.ppk', '-o', 'KbdInteractiveAuthentication=no', '-o', 'PreferredAuthentications=gssapi-with-mic,gssapi-keyex,hostbased,publickey', '-o', 'PasswordAuthentication=no', '-o', 'ConnectTimeout=10', '128.199.129.6', "/bin/sh -c 'mkdir -p $HOME/.ansible/tmp/ansible-tmp-1443340552.33-50544696409516 && echo $HOME/.ansible/tmp/ansible-tmp-1443340552.33-50544696409516'"]
--- | FAILED => SSH encountered an unknown error. The output was:
unknown option -- -
usage: ssh [-1246AaCfgKkMNnqsTtVvXxYy] [-b bind_address] [-c cipher_spec]
           [-D [bind_address:]port] [-E log_file] [-e escape_char]
           [-F configfile] [-I pkcs11] [-i identity_file]
           [-L [bind_address:]port:host:hostport] [-l login_name] [-m mac_spec]
           [-O ctl_cmd] [-o option] [-p port]
           [-Q cipher | cipher-auth | mac | kex | key]
           [-R [bind_address:]port:host:hostport] [-S ctl_path] [-W host:port]
           [-w local_tun[:remote_tun]] [user@]hostname [command]

Enter passphrase for key '.ppk/user.ppk':
Enter passphrase for key '.ppk/user.ppk':
Enter passphrase for key '.ppk/user.ppk':
jbox1-host.promethost.com | FAILED => SSH encountered an unknown error. The output was:
OpenSSH_6.6.1, OpenSSL 1.0.1f 6 Jan 2014
debug1: Reading configuration data /etc/ssh/ssh_config
debug1: /etc/ssh/ssh_config line 19: Applying options for *
debug1: auto-mux: Trying existing master
debug1: Control socket "/root/.ansible/cp/ansible-ssh-128.199.129.6-22-root" does not exist
debug2: ssh_connect: needpriv 0
debug1: Connecting to 128.199.129.6 [128.199.129.6] port 22.
debug2: fd 3 setting O_NONBLOCK
debug1: fd 3 clearing O_NONBLOCK
debug1: Connection established.
debug3: timeout: 9999 ms remain after connect
debug1: permanently_set_uid: 0/0
debug3: Incorrect RSA1 identifier
debug3: Could not load ".ppk/neil_tr.ppk" as a RSA1 public key
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug3: key_read: missing whitespace
debug1: identity file .ppk/neil_tr.ppk type -1
debug1: identity file .ppk/neil_tr.ppk-cert type -1
debug1: Enabling compatibility mode for protocol 2.0
debug1: Local version string SSH-2.0-OpenSSH_6.6.1p1 Ubuntu-2ubuntu2
debug1: Remote protocol version 2.0, remote software version OpenSSH_6.4
debug1: match: OpenSSH_6.4 pat OpenSSH* compat 0x04000000
debug2: fd 3 setting O_NONBLOCK
debug3: load_hostkeys: loading entries for host "128.199.129.6" from file "/root/.ssh/known_hosts"
debug3: load_hostkeys: found key type ECDSA in file /root/.ssh/known_hosts:1
debug3: load_hostkeys: loaded 1 keys
debug3: order_hostkeyalgs: prefer hostkeyalgs: ecdsa-sha2-nis...@openssh.com,ecdsa-sha2-nis...@openssh.com,ecdsa-sha2-nis...@openssh.com,ecdsa-sha2-nistp256,ecdsa-sha2-nistp384,ecdsa-sha2-nistp521
debug1: SSH2_MSG_KEXINIT sent
debug1: SSH2_MSG_KEXINIT received
debug2: kex_parse_kexinit: curve255...@libssh.org,ecdh-sha2-nistp256,ecdh-sha2-nistp384,ecdh-sha2-nistp521,diffie-hellman-group-exchange-sha256,diffie-hellman-group-exchange-sha1,diffie-hellman-group14-sha1,diffie-hellman-group1-sha1
debug2: kex_parse_kexinit: ecdsa-sha2-nis...@openssh.com,ecdsa-sha2-nis...@openssh.com,ecdsa-sha2-nis...@openssh.com,ecdsa-sha2-nistp256,ecdsa-sha2-nistp384,ecdsa-sha2-nistp521,ssh-ed2551...@openssh.com,ssh-rsa-...@openssh.com,ssh-dss-...@openssh.com,ssh-rsa-...@openssh.com,ssh-dss-...@openssh.com,ssh-ed25519,ssh-rsa,ssh-dss
debug2: kex_parse_kexinit: aes128-ctr,aes192-ctr,aes256-ctr,arcfour256,arcfour128,aes12...@openssh.com,aes25...@openssh.com,chacha20...@openssh.com,aes128-cbc,3des-cbc,blowfish-cbc,cast128-cbc,aes192-cbc,aes256-cbc,arcfour,rijnda...@lysator.liu.se
debug2: kex_parse_kexinit: aes128-ctr,aes192-ctr,aes256-ctr,arcfour256,arcfour128,aes12...@openssh.com,aes25...@openssh.com,chacha20...@openssh.com,aes128-cbc,3des-cbc,blowfish-cbc,cast128-cbc,aes192-cbc,aes256-cbc,arcfour,rijnda...@lysator.liu.se
debug2: kex_parse_kexinit: hmac-m...@openssh.com,hmac-s...@openssh.com,umac-...@openssh.com,umac-1...@openssh.com,hmac-sha...@openssh.com,hmac-sha...@openssh.com,hmac-ripe...@openssh.com,hmac-sha...@openssh.com,hmac-md...@openssh.com,hmac-md5,hmac-sha1,uma...@openssh.com,umac...@openssh.com,hmac-sha2-256,hmac-sha2-512,hmac-ripemd160,hmac-ri...@openssh.com,hmac-sha1-96,hmac-md5-96
debug2: kex_parse_kexinit: hmac-m...@openssh.com,hmac-s...@openssh.com,umac-...@openssh.com,umac-1...@openssh.com,hmac-sha...@openssh.com,hmac-sha...@openssh.com,hmac-ripe...@openssh.com,hmac-sha...@openssh.com,hmac-md...@openssh.com,hmac-md5,hmac-sha1,uma...@openssh.com,umac...@openssh.com,hmac-sha2-256,hmac-sha2-512,hmac-ripemd160,hmac-ri...@openssh.com,hmac-sha1-96,hmac-md5-96
debug2: kex_parse_kexinit: zl...@openssh.com,zlib,none
debug2: kex_parse_kexinit: zl...@openssh.com,zlib,none
debug2: kex_parse_kexinit:
debug2: kex_parse_kexinit:
debug2: kex_parse_kexinit: first_kex_follows 0
debug2: kex_parse_kexinit: reserved 0
debug2: kex_parse_kexinit: ecdh-sha2-nistp256,ecdh-sha2-nistp384,ecdh-sha2-nistp521,diffie-hellman-group-exchange-sha256,diffie-hellman-group-exchange-sha1,diffie-hellman-group14-sha1,diffie-hellman-group1-sha1
debug2: kex_parse_kexinit: ssh-rsa,ecdsa-sha2-nistp256
debug2: kex_parse_kexinit: aes128-ctr,aes192-ctr,aes256-ctr,arcfour256,arcfour128,aes12...@openssh.com,aes25...@openssh.com,aes128-cbc,3des-cbc,blowfish-cbc,cast128-cbc,aes192-cbc,aes256-cbc,arcfour,rijnda...@lysator.liu.se
debug2: kex_parse_kexinit: aes128-ctr,aes192-ctr,aes256-ctr,arcfour256,arcfour128,aes12...@openssh.com,aes25...@openssh.com,aes128-cbc,3des-cbc,blowfish-cbc,cast128-cbc,aes192-cbc,aes256-cbc,arcfour,rijnda...@lysator.liu.se
debug2: kex_parse_kexinit: hmac-m...@openssh.com,hmac-s...@openssh.com,umac-...@openssh.com,umac-1...@openssh.com,hmac-sha...@openssh.com,hmac-sha...@openssh.com,hmac-ripe...@openssh.com,hmac-sha...@openssh.com,hmac-md...@openssh.com,hmac-md5,hmac-sha1,uma...@openssh.com,umac...@openssh.com,hmac-sha2-256,hmac-sha2-512,hmac-ripemd160,hmac-ri...@openssh.com,hmac-sha1-96,hmac-md5-96
debug2: kex_parse_kexinit: hmac-m...@openssh.com,hmac-s...@openssh.com,umac-...@openssh.com,umac-1...@openssh.com,hmac-sha...@openssh.com,hmac-sha...@openssh.com,hmac-ripe...@openssh.com,hmac-sha...@openssh.com,hmac-md...@openssh.com,hmac-md5,hmac-sha1,uma...@openssh.com,umac...@openssh.com,hmac-sha2-256,hmac-sha2-512,hmac-ripemd160,hmac-ri...@openssh.com,hmac-sha1-96,hmac-md5-96
debug2: kex_parse_kexinit: none,zl...@openssh.com
debug2: kex_parse_kexinit: none,zl...@openssh.com
debug2: kex_parse_kexinit:
debug2: kex_parse_kexinit:
debug2: kex_parse_kexinit: first_kex_follows 0
debug2: kex_parse_kexinit: reserved 0
debug2: mac_setup: setup hmac-m...@openssh.com
debug1: kex: server->client aes128-ctr hmac-m...@openssh.com zl...@openssh.com
debug2: mac_setup: setup hmac-m...@openssh.com
debug1: kex: client->server aes128-ctr hmac-m...@openssh.com zl...@openssh.com
debug1: sending SSH2_MSG_KEX_ECDH_INIT
debug1: expecting SSH2_MSG_KEX_ECDH_REPLY
debug1: Server host key: ECDSA d3:de:42:d7:d0:e5:d3:60:51:a8:0c:50:69:7c:60:1c
debug3: load_hostkeys: loading entries for host "128.199.129.6" from file "/root/.ssh/known_hosts"
debug3: load_hostkeys: found key type ECDSA in file /root/.ssh/known_hosts:1
debug3: load_hostkeys: loaded 1 keys
debug1: Host '128.199.129.6' is known and matches the ECDSA host key.
debug1: Found key in /root/.ssh/known_hosts:1
debug1: ssh_ecdsa_verify: signature correct
debug2: kex_derive_keys
debug2: set_newkeys: mode 1
debug1: SSH2_MSG_NEWKEYS sent
debug1: expecting SSH2_MSG_NEWKEYS
debug2: set_newkeys: mode 0
debug1: SSH2_MSG_NEWKEYS received
debug1: Roaming not allowed by server
debug1: SSH2_MSG_SERVICE_REQUEST sent
debug2: service_accept: ssh-userauth
debug1: SSH2_MSG_SERVICE_ACCEPT received
debug2: key: .ppk/neil_tr.ppk ((nil)), explicit
debug1: Authentications that can continue: publickey,gssapi-keyex,gssapi-with-mic,password
debug3: start over, passed a different list publickey,gssapi-keyex,gssapi-with-mic,password
debug3: preferred gssapi-with-mic,gssapi-keyex,hostbased,publickey
debug3: authmethod_lookup gssapi-with-mic
debug3: remaining preferred: gssapi-keyex,hostbased,publickey
debug3: authmethod_is_enabled gssapi-with-mic
debug1: Next authentication method: gssapi-with-mic
debug1: Unspecified GSS failure.  Minor code may provide more information
No Kerberos credentials available

debug1: Unspecified GSS failure.  Minor code may provide more information
No Kerberos credentials available

debug1: Unspecified GSS failure.  Minor code may provide more information


debug1: Unspecified GSS failure.  Minor code may provide more information
No Kerberos credentials available

debug2: we did not send a packet, disable method
debug3: authmethod_lookup gssapi-keyex
debug3: remaining preferred: hostbased,publickey
debug3: authmethod_is_enabled gssapi-keyex
debug1: Next authentication method: gssapi-keyex
debug1: No valid Key exchange context
debug2: we did not send a packet, disable method
debug3: authmethod_lookup publickey
debug3: remaining preferred: ,publickey
debug3: authmethod_is_enabled publickey
debug1: Next authentication method: publickey
debug1: Trying private key: .ppk/neil_tr.ppk
debug1: key_parse_private2: missing begin marker
debug1: key_parse_private_pem: PEM_read_PrivateKey failed
debug1: read PEM private key done: type <unknown>
debug1: key_parse_private2: missing begin marker
debug1: key_parse_private_pem: PEM_read_PrivateKey failed
debug1: read PEM private key done: type <unknown>
debug2: bad passphrase given, try again...
debug1: key_parse_private2: missing begin marker
debug1: key_parse_private_pem: PEM_read_PrivateKey failed
debug1: read PEM private key done: type <unknown>
debug2: bad passphrase given, try again...
debug1: key_parse_private2: missing begin marker
debug1: key_parse_private_pem: PEM_read_PrivateKey failed
debug1: read PEM private key done: type <unknown>
debug2: bad passphrase given, try again...
debug2: we did not send a packet, disable method
debug1: No more authentication methods to try.
Permission denied (publickey,gssapi-keyex,gssapi-with-mic,password).

I made sure to place the pass phrase corretly. Any other reason why I am bumping to this?
Also that error that says "debug3: key_read: missing whitespace" seems to be an issue on parsing cause the ppk works prior to encryption.

[Brian Coca]

vault currently only supports yaml data files, your private key is not
being decrypted with vault and you are passing the encrypted/base64
encoded version to ssh


--
Brian Coca