sftp prompts suddenly password after setting authorized_keys from linux to windows which was working for long time

[KNazeerAhamed]

Prerequisites

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• Make sure you are able to repro it on the latest version
• Search the existing issues.

Steps to reproduce

sftp prompts suddenly password after setting authorized_keys from linux to windows which was working for long time

Expected behavior

It should connect without password

Actual behavior

But keep on asking password after setting up the authorized_keys in the remote server which is windows.

Error details

No response

Environment data

PS C:\Users\prv_nazeer> $PSVersionTable

Name                           Value
----                           -----
PSVersion                      5.1.17763.4644
PSEdition                      Desktop
PSCompatibleVersions           {1.0, 2.0, 3.0, 4.0...}
BuildVersion                   10.0.17763.4644
CLRVersion                     4.0.30319.42000
WSManStackVersion              3.0
PSRemotingProtocolVersion      2.3
SerializationVersion           1.1.0.1

Version

OpenSSH_8.0p1

Visuals

No response

[tgauth]

Is it still OpenSSH 8.0 or has it been updated to OpenSSH 9.5? Is it an admin or non-admin user?
If it is an administrator account and using OpenSSH 9.5, the key will need to be in administrators_authorized_keys unless the default sshd_config file has been modified.

If that doesn't work, can you provide the log files? Instructions to retrieve the log files can be found at: https://github.com/PowerShell/Win32-OpenSSH/wiki/Troubleshooting-Steps

[KNazeerAhamed]

Below is the debug from Linux server connect to Windows server.

ssh -vvv svcs_sftp_els@edcfcsn1.esh.ae
OpenSSH_8.0p1, OpenSSL 1.1.1g FIPS 21 Apr 2020
debug1: Reading configuration data /etc/ssh/ssh_config
debug3: /etc/ssh/ssh_config line 52: Including file /etc/ssh/ssh_config.d/05-redhat.conf depth 0
debug1: Reading configuration data /etc/ssh/ssh_config.d/05-redhat.conf
debug2: checking match for 'final all' host edcfcsn1.esh.ae originally edcfcsn1.esh.ae
debug3: /etc/ssh/ssh_config.d/05-redhat.conf line 3: not matched 'final'
debug2: match not found
debug3: /etc/ssh/ssh_config.d/05-redhat.conf line 5: Including file /etc/crypto-policies/back-ends/openssh.config depth 1 (parse only)
debug1: Reading configuration data /etc/crypto-policies/back-ends/openssh.config
debug3: gss kex names ok: [gss-curve25519-sha256-,gss-nistp256-sha256-,gss-group14-sha256-,gss-group16-sha512-,gss-gex-sha1-,gss-group14-sha1-]
debug3: kex names ok: [curve25519-sha256,curve25519-sha256@libssh.org,ecdh-sha2-nistp256,ecdh-sha2-nistp384,ecdh-sha2-nistp521,diffie-hellman-group-exchange-sha256,diffie-hellman-group14-sha256,diffie-hellman-group16-sha512,diffie-hellman-group18-sha512,diffie-hellman-group-exchange-sha1,diffie-hellman-group14-sha1]
debug1: configuration requests final Match pass
debug1: re-parsing configuration
debug1: Reading configuration data /etc/ssh/ssh_config
debug3: /etc/ssh/ssh_config line 52: Including file /etc/ssh/ssh_config.d/05-redhat.conf depth 0
debug1: Reading configuration data /etc/ssh/ssh_config.d/05-redhat.conf
debug2: checking match for 'final all' host edcfcsn1.esh.ae originally edcfcsn1.esh.ae
debug3: /etc/ssh/ssh_config.d/05-redhat.conf line 3: matched 'final'
debug2: match found
debug3: /etc/ssh/ssh_config.d/05-redhat.conf line 5: Including file /etc/crypto-policies/back-ends/openssh.config depth 1
debug1: Reading configuration data /etc/crypto-policies/back-ends/openssh.config
debug3: gss kex names ok: [gss-curve25519-sha256-,gss-nistp256-sha256-,gss-group14-sha256-,gss-group16-sha512-,gss-gex-sha1-,gss-group14-sha1-]
debug3: kex names ok: [curve25519-sha256,curve25519-sha256@libssh.org,ecdh-sha2-nistp256,ecdh-sha2-nistp384,ecdh-sha2-nistp521,diffie-hellman-group-exchange-sha256,diffie-hellman-group14-sha256,diffie-hellman-group16-sha512,diffie-hellman-group18-sha512,diffie-hellman-group-exchange-sha1,diffie-hellman-group14-sha1]
debug2: resolving "edcfcsn1.esh.ae" port 22
debug2: ssh_connect_direct
debug1: Connecting to edcfcsn1.esh.ae [172.16.51.10] port 22.
debug1: Connection established.
debug1: identity file /home/smcmgr/.ssh/id_rsa type 0
debug1: identity file /home/smcmgr/.ssh/id_rsa-cert type -1
debug1: identity file /home/smcmgr/.ssh/id_dsa type -1
debug1: identity file /home/smcmgr/.ssh/id_dsa-cert type -1
debug1: identity file /home/smcmgr/.ssh/id_ecdsa type -1
debug1: identity file /home/smcmgr/.ssh/id_ecdsa-cert type -1
debug1: identity file /home/smcmgr/.ssh/id_ed25519 type -1
debug1: identity file /home/smcmgr/.ssh/id_ed25519-cert type -1
debug1: identity file /home/smcmgr/.ssh/id_xmss type -1
debug1: identity file /home/smcmgr/.ssh/id_xmss-cert type -1
debug1: Local version string SSH-2.0-OpenSSH_8.0
debug1: Remote protocol version 2.0, remote software version OpenSSH_for_Windows_9.1
debug1: match: OpenSSH_for_Windows_9.1 pat OpenSSH* compat 0x04000000
debug2: fd 4 setting O_NONBLOCK
debug1: Authenticating to edcfcsn1.esh.ae:22 as 'svcs_sftp_els'
debug3: hostkeys_foreach: reading file "/home/smcmgr/.ssh/known_hosts"
debug3: record_hostkey: found key type ECDSA in file /home/smcmgr/.ssh/known_hosts:4
debug3: load_hostkeys: loaded 1 keys from edcfcsn1.esh.ae
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-group14-sha256,diffie-hellman-group16-sha512,diffie-hellman-group18-sha512,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,rsa-sha2-512-cert-v01@openssh.com,rsa-sha2-256-cert-v01@openssh.com,ssh-rsa-cert-v01@openssh.com,ssh-ed25519,rsa-sha2-512,rsa-sha2-256,ssh-rsa
debug2: ciphers ctos: aes256-gcm@openssh.com,chacha20-poly1305@openssh.com,aes256-ctr,aes256-cbc,aes128-gcm@openssh.com,aes128-ctr,aes128-cbc
debug2: ciphers stoc: aes256-gcm@openssh.com,chacha20-poly1305@openssh.com,aes256-ctr,aes256-cbc,aes128-gcm@openssh.com,aes128-ctr,aes128-cbc
debug2: MACs ctos: hmac-sha2-256-etm@openssh.com,hmac-sha1-etm@openssh.com,umac-128-etm@openssh.com,hmac-sha2-512-etm@openssh.com,hmac-sha2-256,hmac-sha1,umac-128@openssh.com,hmac-sha2-512
debug2: MACs stoc: hmac-sha2-256-etm@openssh.com,hmac-sha1-etm@openssh.com,umac-128-etm@openssh.com,hmac-sha2-512-etm@openssh.com,hmac-sha2-256,hmac-sha1,umac-128@openssh.com,hmac-sha2-512
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
debug2: host key algorithms: rsa-sha2-512,rsa-sha2-256,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: aes256-gcm@openssh.com MAC: compression: none
debug1: kex: client->server cipher: aes256-gcm@openssh.com MAC: compression: none
debug1: kex: curve25519-sha256 need=32 dh_need=32
debug1: kex: curve25519-sha256 need=32 dh_need=32
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:Ck+PgMM71Hwmo2x/SJ0vd4uW/mZJlidf8ri2LpKXABw
debug3: hostkeys_foreach: reading file "/home/smcmgr/.ssh/known_hosts"
debug3: record_hostkey: found key type ECDSA in file /home/smcmgr/.ssh/known_hosts:4
debug3: load_hostkeys: loaded 1 keys from edcfcsn1.esh.ae
debug3: hostkeys_foreach: reading file "/home/smcmgr/.ssh/known_hosts"
debug3: record_hostkey: found key type ECDSA in file /home/smcmgr/.ssh/known_hosts:4
debug3: load_hostkeys: loaded 1 keys from 172.16.51.10
debug1: Host 'edcfcsn1.esh.ae' is known and matches the ECDSA host key.
debug1: Found key in /home/smcmgr/.ssh/known_hosts:4
debug3: send packet: type 21
debug2: set_newkeys: mode 1
debug1: rekey out after 4294967296 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 in after 4294967296 blocks
debug1: Will attempt key: /home/smcmgr/.ssh/id_rsa RSA SHA256:TGUd6bMv0sGNMlhwccE09ENb5nOsK5YUgISnz9sm8NM
debug1: Will attempt key: /home/smcmgr/.ssh/id_dsa
debug1: Will attempt key: /home/smcmgr/.ssh/id_ecdsa
debug1: Will attempt key: /home/smcmgr/.ssh/id_ed25519
debug1: Will attempt key: /home/smcmgr/.ssh/id_xmss
debug2: pubkey_prepare: done
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,sk-ssh-ed25519@openssh.com,ssh-rsa,rsa-sha2-256,rsa-sha2-512,ssh-dss,ecdsa-sha2-nistp256,ecdsa-sha2-nistp384,ecdsa-sha2-nistp521,sk-ecdsa-sha2-nistp256@openssh.com,webauthn-sk-ecdsa-sha2-nistp256@openssh.com>
debug1: kex_input_ext_info: publickey-hostbound@openssh.com (unrecognised)
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,keyboard-interactive
debug3: start over, passed a different list publickey,password,keyboard-interactive
debug3: preferred 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 public key: /home/smcmgr/.ssh/id_rsa RSA SHA256:TGUd6bMv0sGNMlhwccE09ENb5nOsK5YUgISnz9sm8NM
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,keyboard-interactive
debug1: Trying private key: /home/smcmgr/.ssh/id_dsa
debug3: no such identity: /home/smcmgr/.ssh/id_dsa: No such file or directory
debug1: Trying private key: /home/smcmgr/.ssh/id_ecdsa
debug3: no such identity: /home/smcmgr/.ssh/id_ecdsa: No such file or directory
debug1: Trying private key: /home/smcmgr/.ssh/id_ed25519
debug3: no such identity: /home/smcmgr/.ssh/id_ed25519: No such file or directory
debug1: Trying private key: /home/smcmgr/.ssh/id_xmss
debug3: no such identity: /home/smcmgr/.ssh/id_xmss: 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,password,keyboard-interactive
debug3: userauth_kbdint: disable: no info_req_seen
debug2: we did not send a packet, disable method
debug3: authmethod_lookup password
debug3: remaining preferred:
debug3: authmethod_is_enabled password
debug1: Next authentication method: password
svcs_sftp_els@edcfcsn1.esh.ae's password:

[tgauth]

Thanks - looks like the SSH server is rejecting the RSA key. Are you able to pull the SSH server logs?