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Unable to SSH into Windows 2016 OpenSSH Server until login once #1562

Open neoanantha opened 4 years ago

neoanantha commented 4 years ago

"OpenSSH for Windows" version OpenSSH_8.1p1 for Windows

Server OperatingSystem Windows Server 2016

Client OperatingSystem CentOS Linux release 7.7.1908 (Core) Linux 3.10.0-1062.el7.x86_64 #1 SMP Wed Aug 7 18:08:02 UTC 2019 x86_64 x86_64 x86_64 GNU/Linux

What is failing ssh connection to OpenSSH Server running on Windows Server 2016 from Linux is failing until user logs into the Windows Server once through the user being used for ssh connection

Steps to reproduce Enable pubkey auth from CentOS 7 client machine to OpenSSH server Windows Server 2016

The user is "adminuser" which is part of administrators group on Windows Server 2016 and it's auth...keys is located at C:\Users\adminuser.ssh\authorized_keys

Windows Server goes for a restart. Once Windows server reboots and shows login screen, DO NOT login into windows using adminuser

Go back to linux shell and attempt to do plain ssh "ssh adminuser@windowsserver" from CentOS7 client machine

Moving authorized_keys to some other location like C:\openssh.ssh did not help either, of course the path was updated accordingly in c:\programdata\ssh\sshd_config, which this step was attempted

btw this machine is part of AD

Expected output ssh connection should get established

Actual output ssh connection fails with permission denied

Success scenario Login into Windows 2016 system through the login screen using "adminuser"

Come back to CentOS7 client machine and run the "ssh adminuser@windowsserver"

Immediately ssh connection gets established successfully

Logs when adminuser is not logged into Windows Server 2016-ssh failed

OpenSSH_7.4p1, OpenSSL 1.0.2k-fips  26 Jan 2017
debug1: Reading configuration data /etc/ssh/ssh_config
debug1: /etc/ssh/ssh_config line 58: Applying options for *
debug2: resolving "192.168.1.201" port 22
debug2: ssh_connect_direct: needpriv 0
debug1: Connecting to 192.168.1.201 [192.168.1.201] port 22.
debug1: Connection established.
debug1: permanently_set_uid: 0/0
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: Enabling compatibility mode for protocol 2.0
debug1: Local version string SSH-2.0-OpenSSH_7.4
debug1: Remote protocol version 2.0, remote software version OpenSSH_for_Windows_8.1
debug1: match: OpenSSH_for_Windows_8.1 pat OpenSSH* compat 0x04000000
debug2: fd 3 setting O_NONBLOCK
debug1: Authenticating to 192.168.1.201:22 as 'cceuser'
debug3: hostkeys_foreach: reading file "/root/.ssh/known_hosts"
debug3: record_hostkey: found key type ECDSA in file /root/.ssh/known_hosts:2
debug3: load_hostkeys: loaded 1 keys from 192.168.1.201
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,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,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-dss-cert-v01@openssh.com,ssh-ed25519,rsa-sha2-512,rsa-sha2-256,ssh-rsa,ssh-dss
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
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
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-group14-sha256,diffie-hellman-group14-sha1
debug2: host key algorithms: rsa-sha2-512,rsa-sha2-256,ssh-rsa,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
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
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: kex: curve25519-sha256 need=64 dh_need=64
debug1: kex: curve25519-sha256 need=64 dh_need=64
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:EwYuZnUFYsv8UTiIQlT1L5IbRM/+DHs3Av83mPF9BdA
debug3: hostkeys_foreach: reading file "/root/.ssh/known_hosts"
debug3: record_hostkey: found key type ECDSA in file /root/.ssh/known_hosts:2
debug3: load_hostkeys: loaded 1 keys from 192.168.1.201
debug1: Host '192.168.1.201' is known and matches the ECDSA host key.
debug1: Found key in /root/.ssh/known_hosts:2
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 (0x55f84af33910)
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=<ssh-ed25519,ssh-rsa,rsa-sha2-256,rsa-sha2-512,ssh-dss,ecdsa-sha2-nistp256,ecdsa-sha2-nistp384,ecdsa-sha2-nistp521>
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,keyboard-interactive
debug3: start over, passed a different list publickey,keyboard-interactive
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: Offering RSA public key: /root/.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,keyboard-interactive
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
debug3: authmethod_lookup keyboard-interactive
debug3: remaining preferred: password
debug3: authmethod_is_enabled keyboard-interactive
debug1: Next authentication method: keyboard-interactive
debug2: userauth_kbdint
debug3: send packet: type 50
debug2: we sent a keyboard-interactive packet, wait for reply
debug3: receive packet: type 51
debug1: Authentications that can continue: publickey,keyboard-interactive
debug3: userauth_kbdint: disable: no info_req_seen
debug2: we did not send a packet, disable method
debug1: No more authentication methods to try.
Permission denied (publickey,keyboard-interactive).

Logs after adminuser logged into Windows Server 2016 through windows console

OpenSSH_7.4p1, OpenSSL 1.0.2k-fips  26 Jan 2017
debug1: Reading configuration data /etc/ssh/ssh_config
debug1: /etc/ssh/ssh_config line 58: Applying options for *
debug2: resolving "192.168.1.201" port 22
debug2: ssh_connect_direct: needpriv 0
debug1: Connecting to 192.168.1.201 [192.168.1.201] port 22.
debug1: Connection established.
debug1: permanently_set_uid: 0/0
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: Enabling compatibility mode for protocol 2.0
debug1: Local version string SSH-2.0-OpenSSH_7.4
debug1: Remote protocol version 2.0, remote software version OpenSSH_for_Windows_8.1
debug1: match: OpenSSH_for_Windows_8.1 pat OpenSSH* compat 0x04000000
debug2: fd 3 setting O_NONBLOCK
debug1: Authenticating to 192.168.1.201:22 as 'cceuser'
debug3: hostkeys_foreach: reading file "/root/.ssh/known_hosts"
debug3: record_hostkey: found key type ECDSA in file /root/.ssh/known_hosts:2
debug3: load_hostkeys: loaded 1 keys from 192.168.1.201
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,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,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-dss-cert-v01@openssh.com,ssh-ed25519,rsa-sha2-512,rsa-sha2-256,ssh-rsa,ssh-dss
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
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
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-group14-sha256,diffie-hellman-group14-sha1
debug2: host key algorithms: rsa-sha2-512,rsa-sha2-256,ssh-rsa,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
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
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: kex: curve25519-sha256 need=64 dh_need=64
debug1: kex: curve25519-sha256 need=64 dh_need=64
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:EwYuZnUFYsv8UTiIQlT1L5IbRM/+DHs3Av83mPF9BdA
debug3: hostkeys_foreach: reading file "/root/.ssh/known_hosts"
debug3: record_hostkey: found key type ECDSA in file /root/.ssh/known_hosts:2
debug3: load_hostkeys: loaded 1 keys from 192.168.1.201
debug1: Host '192.168.1.201' is known and matches the ECDSA host key.
debug1: Found key in /root/.ssh/known_hosts:2
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 (0x55db6b645910)
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=<ssh-ed25519,ssh-rsa,rsa-sha2-256,rsa-sha2-512,ssh-dss,ecdsa-sha2-nistp256,ecdsa-sha2-nistp384,ecdsa-sha2-nistp521>
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,keyboard-interactive
debug3: start over, passed a different list publickey,keyboard-interactive
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: Offering RSA public key: /root/.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 60
debug1: Server accepts key: pkalg rsa-sha2-512 blen 279
debug2: input_userauth_pk_ok: fp SHA256:SCufnLjYpdlZZ6JpxJj2ZXZuqBiNQkdkurI7RSukQdA
debug3: sign_and_send_pubkey: RSA SHA256:SCufnLjYpdlZZ6JpxJj2ZXZuqBiNQkdkurI7RSukQdA
debug3: send packet: type 50
debug3: receive packet: type 52
debug1: Authentication succeeded (publickey).
Authenticated to 192.168.1.201 ([192.168.1.201]:22).
debug2: fd 5 setting O_NONBLOCK
debug3: fd 6 is O_NONBLOCK
debug1: channel 0: new [client-session]
debug3: ssh_session2_open: channel_new: 0
debug2: channel 0: send open
debug3: send packet: type 90
debug1: Requesting no-more-sessions@openssh.com
debug3: send packet: type 80
debug1: Entering interactive session.
debug1: pledge: network
debug3: receive packet: type 80
debug1: client_input_global_request: rtype hostkeys-00@openssh.com want_reply 0
debug3: receive packet: type 91
debug2: callback start
debug2: fd 3 setting TCP_NODELAY
debug3: ssh_packet_set_tos: set IP_TOS 0x10
debug2: client_session2_setup: id 0
debug2: channel 0: request pty-req confirm 1
debug3: send packet: type 98
debug1: Sending environment.
debug3: Ignored env XDG_SESSION_ID
debug3: Ignored env HOSTNAME
debug3: Ignored env TERM
debug3: Ignored env SHELL
debug3: Ignored env HISTSIZE
debug3: Ignored env SSH_CLIENT
debug3: Ignored env SSH_TTY
debug3: Ignored env USER
debug3: Ignored env LS_COLORS
debug3: Ignored env MAIL
debug3: Ignored env PATH
debug3: Ignored env PWD
debug1: Sending env LANG = en_US.UTF-8
debug2: channel 0: request env confirm 0
debug3: send packet: type 98
debug3: Ignored env HISTCONTROL
debug3: Ignored env SHLVL
debug3: Ignored env HOME
debug3: Ignored env LOGNAME
debug3: Ignored env SSH_CONNECTION
debug3: Ignored env LESSOPEN
debug3: Ignored env XDG_RUNTIME_DIR
debug3: Ignored env _
debug2: channel 0: request shell confirm 1
debug3: send packet: type 98
debug2: callback done
debug2: channel 0: open confirm rwindow 0 rmax 32768
debug3: receive packet: type 99
debug2: channel_input_status_confirm: type 99 id 0
debug2: PTY allocation request accepted on channel 0
debug2: channel 0: rcvd adjust 2097152
debug3: receive packet: type 99
debug2: channel_input_status_confirm: type 99 id 0
debug2: shell request accepted on channel 0
Windows PowerShell
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PS C:\Users\cceuser> exit
debug3: receive packet: type 96
debug2: channel 0: rcvd eof
debug2: channel 0: output open -> drain
debug2: channel 0: obuf empty
debug2: channel 0: close_write
debug2: channel 0: output drain -> closed
debug3: receive packet: type 98
debug1: client_input_channel_req: channel 0 rtype exit-status reply 0
debug3: receive packet: type 97
debug2: channel 0: rcvd close
debug2: channel 0: close_read
debug2: channel 0: input open -> closed
debug3: channel 0: will not send data after close
debug2: channel 0: almost dead
debug2: channel 0: gc: notify user
debug2: channel 0: gc: user detached
debug2: channel 0: send close
debug3: send packet: type 97
debug2: channel 0: is dead
debug2: channel 0: garbage collecting
debug1: channel 0: free: client-session, nchannels 1
debug3: channel 0: status: The following connections are open:
  #0 client-session (t4 r0 i3/0 o3/0 fd -1/-1 cc -1)

debug3: send packet: type 1
debug1: fd 1 clearing O_NONBLOCK
debug3: fd 2 is not O_NONBLOCK
Connection to 192.168.1.201 closed.
Transferred: sent 3272, received 5616 bytes, in 14.2 seconds
Bytes per second: sent 230.7, received 395.9
debug1: Exit status 0

Eventhough we are using Win32-OpenSSH with ansible, issue and resolution mentioned in this link was not applicable in my case

https://github.com/ansible/ansible/issues/62730

Steps which solved the issue in above ansible issue was tried but didn't help in resolving the problem

subflow22 commented 4 years ago

I have recently encountered the same behavior while creating Packer images using the same OS for AWS. The user data I supply configures SSH similar to what you have done. I recieve permission denied but if I interactively log in as Administrator, ssh is immediately available.

My resolution was simply to wait. Whatever was accomplished by my logon eventually occurs regardless and I can successfully connect via ssh.

neoanantha commented 4 years ago

Thanks for sharing your experience @subflow22

It was an internal automation setup.

Hence loaded up username and password plaintext into registry to automatic login for now as it was a sandbox testbed without access to external network

SSH is working fine and that is doing the job for now

Testbed is under continuous use now. Will try your solution when it becomes free and revert back here with results