Ssh/scp - Permission denied (publickey,password)

Question

I have an Ubuntu VM set up on my Mac that I would like to copy files into, however I keep getting permission denied and eventually Permission denied (publickey,password) errors. I have opened up the vm and I know that ssh-server is installed, and I can ping the address from my host machine. I tried copying my public key from ~/.ssh/id_rsa.pub into home/osboxes/.ssh/authorized_keys on the vm but this also did not seem to make a difference.

Does anyone have a suggestion as to what might be going wrong? I ran it with the -vvv flag and it says the packet response to the password authorisations is receive packet: type 51 .

ssh -vvv osboxes@192.168.1.11
OpenSSH_7.2p2, LibreSSL 2.4.1
debug1: Reading configuration data /etc/ssh/ssh_config
debug1: /etc/ssh/ssh_config line 20: Applying options for *
debug1: /etc/ssh/ssh_config line 102: Applying options for *
debug2: resolving "192.168.1.11" port 22
debug2: ssh_connect_direct: needpriv 0
debug1: Connecting to 192.168.1.11 [192.168.1.11] port 22.
debug1: Connection established.
debug1: identity file /Users/annecope/.ssh/id_rsa type 1
debug1: key_load_public: No such file or directory
debug1: identity file /Users/annecope/.ssh/id_rsa-cert type -1
debug1: key_load_public: No such file or directory
debug1: identity file /Users/annecope/.ssh/id_dsa type -1
debug1: key_load_public: No such file or directory
debug1: identity file /Users/annecope/.ssh/id_dsa-cert type -1
debug1: key_load_public: No such file or directory
debug1: identity file /Users/annecope/.ssh/id_ecdsa type -1
debug1: key_load_public: No such file or directory
debug1: identity file /Users/annecope/.ssh/id_ecdsa-cert type -1
debug1: key_load_public: No such file or directory
debug1: identity file /Users/annecope/.ssh/id_ed25519 type -1
debug1: key_load_public: No such file or directory
debug1: identity file /Users/annecope/.ssh/id_ed25519-cert type -1
debug1: Enabling compatibility mode for protocol 2.0
debug1: Local version string SSH-2.0-OpenSSH_7.2
debug1: Remote protocol version 2.0, remote software version OpenSSH_6.6.1p1 Ubuntu-2ubuntu2.8
debug1: match: OpenSSH_6.6.1p1 Ubuntu-2ubuntu2.8 pat OpenSSH_6.6.1* compat 0x04000000
debug2: fd 3 setting O_NONBLOCK
debug1: Authenticating to 192.168.1.11:22 as 'osboxes'
debug3: hostkeys_foreach: reading file "/Users/annecope/.ssh/known_hosts"
debug3: record_hostkey: found key type ECDSA in file /Users/annecope/.ssh/known_hosts:5
debug3: load_hostkeys: loaded 1 keys from 192.168.1.11
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
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@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,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,ssh-ed25519-cert-v01@openssh.com,ssh-rsa-cert-v01@openssh.com,ssh-ed25519,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,aes128-cbc,aes192-cbc,aes256-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,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,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-group-exchange-sha1,diffie-hellman-group14-sha1,diffie-hellman-group1-sha1
debug2: host key algorithms: ssh-rsa,ssh-dss,ecdsa-sha2-nistp256,ssh-ed25519
debug2: ciphers ctos: 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: ciphers stoc: 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: MACs ctos: 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: MACs stoc: 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: 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: 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
debug3: send packet: type 30
debug1: expecting SSH2_MSG_KEX_ECDH_REPLY
debug3: receive packet: type 31
debug1: Server host key: ecdsa-sha2-nistp256 SHA256:o3ZMpLaE6l8euGTM87PY9S+1tfuWRlSf6cki0RJYtUE
debug3: hostkeys_foreach: reading file "/Users/annecope/.ssh/known_hosts"
debug3: record_hostkey: found key type ECDSA in file /Users/annecope/.ssh/known_hosts:5
debug3: load_hostkeys: loaded 1 keys from 192.168.1.11
debug1: Host '192.168.1.11' is known and matches the ECDSA host key.
debug1: Found key in /Users/annecope/.ssh/known_hosts:5
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
debug2: set_newkeys: mode 0
debug1: rekey after 134217728 blocks
debug1: SSH2_MSG_NEWKEYS received
debug2: key: /Users/annecope/.ssh/id_rsa (0x7f8123d0ae90)
debug2: key: /Users/annecope/.ssh/id_dsa (0x0)
debug2: key: /Users/annecope/.ssh/id_ecdsa (0x0)
debug2: key: /Users/annecope/.ssh/id_ed25519 (0x0)
debug3: send packet: type 5
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,password
debug3: start over, passed a different list publickey,password
debug3: preferred 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: Offering RSA public key: /Users/annecope/.ssh/id_rsa
debug3: send_pubkey_test
debug3: send packet: type 50
debug2: we sent a publickey packet, wait for reply
debug3: receive packet: type 51
debug1: Authentications that can continue: publickey,password
debug1: Trying private key: /Users/annecope/.ssh/id_dsa
debug3: no such identity: /Users/annecope/.ssh/id_dsa: No such file or directory
debug1: Trying private key: /Users/annecope/.ssh/id_ecdsa
debug3: no such identity: /Users/annecope/.ssh/id_ecdsa: No such file or directory
debug1: Trying private key: /Users/annecope/.ssh/id_ed25519
debug3: no such identity: /Users/annecope/.ssh/id_ed25519: No such file or directory
debug2: we did not send a packet, disable method
debug3: authmethod_lookup password
debug3: remaining preferred: ,password
debug3: authmethod_is_enabled password
debug1: Next authentication method: password
osboxes@192.168.1.11's password: 
debug3: send packet: type 50
debug2: we sent a password packet, wait for reply
debug3: receive packet: type 51
debug1: Authentications that can continue: publickey,password
Permission denied, please try again.
osboxes@192.168.1.11's password: 
debug3: send packet: type 50
debug2: we sent a password packet, wait for reply
debug3: receive packet: type 51
debug1: Authentications that can continue: publickey,password
Permission denied, please try again.
osboxes@192.168.1.11's password: 
debug3: send packet: type 50
debug2: we sent a password packet, wait for reply
debug3: receive packet: type 51
debug1: Authentications that can continue: publickey,password
debug2: we did not send a packet, disable method
debug1: No more authentication methods to try.
Permission denied (publickey,password).

Answer 1

I have had a similar issue and realised that the root login using ssh was disabled.

Ensure that in the SSHD config, you have PermitRootLogin yes

Hope that helps

Answer 2

One of probable complications for this failed authentications is disabled authorized_keys file on server. Sometimes the name is changed or it is disabled with commented line. Configuration is in

/etc/ssh/sshd_config

and example line is:

#AuthorizedKeysFile     %h/.ssh/authorized_keys

Answer 3

SSH does not even know about your key, so it's not even trying to use it. Add your key to the config file, that way the SSH client knows it exists:

First let's make a backup of your config file:

cp ~/.ssh/config ~/.ssh/config-001

Then let's add the key name:

echo -e "\nIdentityFile ~/.ssh/id_rsa" >> ~/.ssh/config