Trouble provisioning remote server with ansible 2.4

Hi roots community, I have another frustrating dilemma and it would be wonderful to have another pair of eyes on this (really any but mine…). I get this error when I try to provision the remote server (even with the --ask-pass option… same error without the option as well).

$sudo ansible-playbook server.yml -e env=staging -u root --ask-pass -vvvv

Failed to connect to the host via ssh: OpenSSH_7.6p1 Ubuntu-4, OpenSSL 1.0.2n
7 Dec 2017
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 "/home/jill/.ansible/cp/4c119164e1" does not exist
debug2: resolving "159.65.244.133" port 22
debug2: ssh_connect_direct: needpriv 0
debug1: Connecting to 159.65.244.133 [159.65.244.133] port 22.
debug2: fd 3 setting O_NONBLOCK
debug1: fd 3 clearing O_NONBLOCK
debug1: Connection established.
debug3: timeout: 9972 ms remain after connect
debug1: permanently_set_uid: 0/0
debug1: key_load_public: No such file or directory
debug1: identity file /root/.ssh/id_rsa type -1
debug1: key_load_public: No such file or directory
debug1: identity file /root/.ssh/id_rsa-cert type -1
debug1: key_load_public: No such file or directory
debug1: identity file /root/.ssh/id_dsa type -1
debug1: key_load_public: No such file or directory
debug1: identity file /root/.ssh/id_dsa-cert type -1
debug1: key_load_public: No such file or directory
debug1: identity file /root/.ssh/id_ecdsa type -1
debug1: key_load_public: No such file or directory
debug1: identity file /root/.ssh/id_ecdsa-cert type -1
debug1: key_load_public: No such file or directory
debug1: identity file /root/.ssh/id_ed25519 type -1
debug1: key_load_public: No such file or directory
debug1: identity file /root/.ssh/id_ed25519-cert type -1
debug1: Local version string SSH-2.0-OpenSSH_7.6p1 Ubuntu-4
debug1: Remote protocol version 2.0, remote software version OpenSSH_7.2p2
Ubuntu-4ubuntu2.8
debug1: match: OpenSSH_7.2p2 Ubuntu-4ubuntu2.8 pat OpenSSH* compat 0x04000000
debug2: fd 3 setting O_NONBLOCK
debug1: Authenticating to 159.65.244.133:22 as 'root'
debug3: hostkeys_foreach: reading file "/root/.ssh/known_hosts"
debug3: record_hostkey: found key type ED25519 in file
/root/.ssh/known_hosts:9
debug3: load_hostkeys: loaded 1 keys from 159.65.244.133
debug3: order_hostkeyalgs: prefer hostkeyalgs: ssh-
ed25519-cert-v01@openssh.com,ssh-ed25519
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-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,ext-info-c
debug2: host key algorithms: ssh-ed25519-cert-v01@openssh.com,ssh-ed25519
,ecdsa-sha2-nistp256-cert-v01@openssh.com,ecdsa-
sha2-nistp384-cert-v01@openssh.com,ecdsa-sha2-nistp521-cert-v01@openssh.com
,ssh-rsa-cert-v01@openssh.com,ecdsa-sha2-nistp256,ecdsa-sha2-nistp384,ecdsa-
sha2-nistp521,rsa-sha2-512,rsa-sha2-256,ssh-rsa
debug2: ciphers ctos: chacha20-poly1305@openssh.com,aes128-ctr,aes192-ctr,aes
256-ctr,aes128-gcm@openssh.com,aes256-gcm@openssh.com
debug2: ciphers stoc: chacha20-poly1305@openssh.com,aes128-ctr,aes192-ctr,aes
256-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@libssh.org,ecdh-sha2-nistp256,ecdh-
sha2-nistp384,ecdh-sha2-nistp521,diffie-hellman-group-exchange-sha256,diffie-
hellman-group14-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,aes
256-ctr,aes128-gcm@openssh.com,aes256-gcm@openssh.com
debug2: ciphers stoc: chacha20-poly1305@openssh.com,aes128-ctr,aes192-ctr,aes
256-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
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@libssh.org
debug1: kex: host key algorithm: ssh-ed25519
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
debug3: send packet: type 30
debug1: expecting SSH2_MSG_KEX_ECDH_REPLY
debug3: receive packet: type 31
debug1: Server host key: ssh-ed25519
SHA256:h5ttXeall7vVdsT+r9GRe6GmAFYozHN5DGjzrfUeRZM
debug3: hostkeys_foreach: reading file "/root/.ssh/known_hosts"
debug3: record_hostkey: found key type ED25519 in file
/root/.ssh/known_hosts:9
debug3: load_hostkeys: loaded 1 keys from 159.65.244.133
debug1: Host '159.65.244.133' is known and matches the ED25519 host key.
debug1: Found key in /root/.ssh/known_hosts:9
debug3: send packet: type 21
debug2: set_newkeys: mode 1
debug1: rekey after 134217728 blocks
debug1: SSH2_MSG_NEWKEYS sent
debug1: expecting SSH2_MSG_NEWKEYS
debug3: receive packet: type 21
debug1: SSH2_MSG_NEWKEYS received
debug2: set_newkeys: mode 0
debug1: rekey after 134217728 blocks
debug2: key: /root/.ssh/id_rsa ((nil))
debug2: key: /root/.ssh/id_dsa ((nil))
debug2: key: /root/.ssh/id_ecdsa ((nil))
debug2: key: /root/.ssh/id_ed25519 ((nil))
debug3: send packet: type 5
debug3: receive packet: type 7
debug1: SSH2_MSG_EXT_INFO received
debug1: kex_input_ext_info: server-sig-algs=<rsa-sha2-256,rsa-sha2-512>
debug3: receive packet: type 6
debug2: service_accept: ssh-userauth
debug1: SSH2_MSG_SERVICE_ACCEPT received
debug3: send packet: type 50
debug3: receive packet: type 51
debug1: Authentications that can continue: publickey
debug3: start over, passed a different list publickey
debug3: preferred gssapi-keyex,gssapi-with-mic,publickey,keyboard-
interactive,password
debug3: authmethod_lookup publickey
debug3: remaining preferred: keyboard-interactive,password
debug3: authmethod_is_enabled publickey
debug1: Next authentication method: publickey
debug1: Trying private key: /root/.ssh/id_rsa
debug3: no such identity: /root/.ssh/id_rsa: No such file or directory
debug1: Trying private key: /root/.ssh/id_dsa
debug3: no such identity: /root/.ssh/id_dsa: No such file or directory
debug1: Trying private key: /root/.ssh/id_ecdsa
debug3: no such identity: /root/.ssh/id_ecdsa: No such file or directory
debug1: Trying private key: /root/.ssh/id_ed25519
debug3: no such identity: /root/.ssh/id_ed25519: No such file or directory
debug2: we did not send a packet, disable method
debug1: No more authentication methods to try.
root@159.65.244.133: Permission denied (publickey).

fatal: [159.65.244.133]: UNREACHABLE! => {
    "changed": false, 
    "unreachable": true
}

This is the error that outputs when I run ansible ping

$ ansible staging -m ping -u root --ask-pass

SSH password: 
159.65.244.133 | FAILED! => {
    "changed": false, 
    "failed": true, 
    "module_stderr": "Shared connection to 159.65.244.133 closed.\r\n", 
    "module_stdout": "/bin/sh: 1: /usr/bin/python: not found\r\n", 
    "msg": "MODULE FAILURE", 
    "rc": 0
}

You may notice it complains about not finding /usr/bin/python, but that file /is / there :c

Let me know if there is any more detail I can provide.
I’m running out of tricks! Please help! Thank you for your advice and assistance!

Why are you running ansible as root? I’m not sure why that would be necessary, and it seems kind of dangerous (and like it could be causing your issue).

At the risk of stating the obvious, it looks like you haven’t loaded an SSH key. The docs have some details on using SSH keys: https://roots.io/trellis/docs/ssh-keys/ I don’t know if Trellis is written to work without SSH keys.