PPK failed to authenticate after encrypting

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-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
debug1: SSH2_MSG_KEXINIT sent
debug1: SSH2_MSG_KEXINIT received
debug2: kex_parse_kexinit: curve25519-sha256@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-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,ssh-ed25519-cert-v01@openssh.com,ssh-rsa-cert-v01@openssh.com,ssh-dss-cert-v01@openssh.com,ssh-rsa-cert-v00@openssh.com,ssh-dss-cert-v00@openssh.com,ssh-ed25519,ssh-rsa,ssh-dss
debug2: kex_parse_kexinit: aes128-ctr,aes192-ctr,aes256-ctr,arcfour256,arcfour128,aes128-gcm@openssh.com,aes256-gcm@openssh.com,chacha20-poly1305@openssh.com,aes128-cbc,3des-cbc,blowfish-cbc,cast128-cbc,aes192-cbc,aes256-cbc,arcfour,rijndael-cbc@lysator.liu.se
debug2: kex_parse_kexinit: aes128-ctr,aes192-ctr,aes256-ctr,arcfour256,arcfour128,aes128-gcm@openssh.com,aes256-gcm@openssh.com,chacha20-poly1305@openssh.com,aes128-cbc,3des-cbc,blowfish-cbc,cast128-cbc,aes192-cbc,aes256-cbc,arcfour,rijndael-cbc@lysator.liu.se
debug2: kex_parse_kexinit: hmac-md5-etm@openssh.com,hmac-sha1-etm@openssh.com,umac-64-etm@openssh.com,umac-128-etm@openssh.com,hmac-sha2-256-etm@openssh.com,hmac-sha2-512-etm@openssh.com,hmac-ripemd160-etm@openssh.com,hmac-sha1-96-etm@openssh.com,hmac-md5-96-etm@openssh.com,hmac-md5,hmac-sha1,umac-64@openssh.com,umac-128@openssh.com,hmac-sha2-256,hmac-sha2-512,hmac-ripemd160,hmac-ripemd160@openssh.com,hmac-sha1-96,hmac-md5-96
debug2: kex_parse_kexinit: hmac-md5-etm@openssh.com,hmac-sha1-etm@openssh.com,umac-64-etm@openssh.com,umac-128-etm@openssh.com,hmac-sha2-256-etm@openssh.com,hmac-sha2-512-etm@openssh.com,hmac-ripemd160-etm@openssh.com,hmac-sha1-96-etm@openssh.com,hmac-md5-96-etm@openssh.com,hmac-md5,hmac-sha1,umac-64@openssh.com,umac-128@openssh.com,hmac-sha2-256,hmac-sha2-512,hmac-ripemd160,hmac-ripemd160@openssh.com,hmac-sha1-96,hmac-md5-96
debug2: kex_parse_kexinit: zlib@openssh.com,zlib,none
debug2: kex_parse_kexinit: zlib@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,aes128-gcm@openssh.com,aes256-gcm@openssh.com,aes128-cbc,3des-cbc,blowfish-cbc,cast128-cbc,aes192-cbc,aes256-cbc,arcfour,rijndael-cbc@lysator.liu.se
debug2: kex_parse_kexinit: aes128-ctr,aes192-ctr,aes256-ctr,arcfour256,arcfour128,aes128-gcm@openssh.com,aes256-gcm@openssh.com,aes128-cbc,3des-cbc,blowfish-cbc,cast128-cbc,aes192-cbc,aes256-cbc,arcfour,rijndael-cbc@lysator.liu.se
debug2: kex_parse_kexinit: hmac-md5-etm@openssh.com,hmac-sha1-etm@openssh.com,umac-64-etm@openssh.com,umac-128-etm@openssh.com,hmac-sha2-256-etm@openssh.com,hmac-sha2-512-etm@openssh.com,hmac-ripemd160-etm@openssh.com,hmac-sha1-96-etm@openssh.com,hmac-md5-96-etm@openssh.com,hmac-md5,hmac-sha1,umac-64@openssh.com,umac-128@openssh.com,hmac-sha2-256,hmac-sha2-512,hmac-ripemd160,hmac-ripemd160@openssh.com,hmac-sha1-96,hmac-md5-96
debug2: kex_parse_kexinit: hmac-md5-etm@openssh.com,hmac-sha1-etm@openssh.com,umac-64-etm@openssh.com,umac-128-etm@openssh.com,hmac-sha2-256-etm@openssh.com,hmac-sha2-512-etm@openssh.com,hmac-ripemd160-etm@openssh.com,hmac-sha1-96-etm@openssh.com,hmac-md5-96-etm@openssh.com,hmac-md5,hmac-sha1,umac-64@openssh.com,umac-128@openssh.com,hmac-sha2-256,hmac-sha2-512,hmac-ripemd160,hmac-ripemd160@openssh.com,hmac-sha1-96,hmac-md5-96
debug2: kex_parse_kexinit: none,zlib@openssh.com
debug2: kex_parse_kexinit: none,zlib@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-md5-etm@openssh.com
debug1: kex: server->client aes128-ctr hmac-md5-etm@openssh.com zlib@openssh.com
debug2: mac_setup: setup hmac-md5-etm@openssh.com
debug1: kex: client->server aes128-ctr hmac-md5-etm@openssh.com zlib@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
debug1: key_parse_private2: missing begin marker
debug1: key_parse_private_pem: PEM_read_PrivateKey failed
debug1: read PEM private key done: type
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
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
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.

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