Further Update
Turns out that it was the Windows server receiving the SSH that was not set up correctly.
Before posting, please read how to report bug or request support effectively.
Bug reports without an attached log file are usually useless.
. 2018-06-27 10:36:12.237 [Tunnel] Opening connection to xxx.xxx.xxx.xxx:22 for forwarding from 127.0.0.1:50553
. 2018-06-27 10:36:12.251 [Tunnel] Forwarded connection refused by server: Connect failed []
. 2018-06-27 10:36:12.503 [Tunnel] Closing connection.
. 2018-06-27 10:36:11.865 Opening tunnel.
. 2018-06-27 10:36:11.881 [Tunnel] Looking up host "xxx.xxx.xxx.xxx" for SSH connection
. 2018-06-27 10:36:11.881 [Tunnel] Connecting to xxx.xxx.xxx.xxx port 22
. 2018-06-27 10:36:11.894 [Tunnel] We claim version: SSH-2.0-WinSCP_release_5.13.1
. 2018-06-27 10:36:11.915 [Tunnel] Server version: SSH-2.0-WeOnlyDo 2.4.3
. 2018-06-27 10:36:11.915 [Tunnel] Using SSH protocol version 2
. 2018-06-27 10:36:11.915 [Tunnel] Have a known host key of type dss
. 2018-06-27 10:36:11.928 [Tunnel] Doing ECDH key exchange with curve nistp256 and hash SHA-256
. 2018-06-27 10:36:12.023 [Tunnel] Host key fingerprint is:
. 2018-06-27 10:36:12.023 [Tunnel] ssh-dss 1024 87:ae:5f:c9:4c:02:96:b1:04:dd:b0:04:31:6b:9d:27 kwLs2HHyixqdVyriERMs+g/mW7VlEn1S4NOG4MTZ+xo=
. 2018-06-27 10:36:12.070 [Tunnel] Host key matches cached key
. 2018-06-27 10:36:12.070 [Tunnel] Initialised AES-256 SDCTR client->server encryption
. 2018-06-27 10:36:12.070 [Tunnel] Initialised HMAC-SHA-256 client->server MAC algorithm
. 2018-06-27 10:36:12.084 [Tunnel] Initialised AES-256 SDCTR server->client encryption
. 2018-06-27 10:36:12.084 [Tunnel] Initialised HMAC-SHA-256 server->client MAC algorithm
. 2018-06-27 10:36:12.113 [Tunnel] Reading key file "xxxxxxxxx.ppk"
. 2018-06-27 10:36:12.113 [Tunnel] Pageant is running. Requesting keys.
. 2018-06-27 10:36:12.114 [Tunnel] Pageant has 1 SSH-2 keys
. 2018-06-27 10:36:12.114 [Tunnel] Pageant key #0 matches configured key file
! 2018-06-27 10:36:12.114 [Tunnel] Using username "xxxxxxx".
. 2018-06-27 10:36:12.148 [Tunnel] Server offered these authentication methods: publickey
. 2018-06-27 10:36:12.149 [Tunnel] Trying Pageant key #0
! 2018-06-27 10:36:12.162 [Tunnel] Authenticating with public key "xxxxxxx" from agent
. 2018-06-27 10:36:12.180 [Tunnel] Sending Pageant's response
. 2018-06-27 10:36:12.195 [Tunnel] Access granted
. 2018-06-27 10:36:12.195 [Tunnel] Local port 50022 forwarding to xxx.xxx.xxx.xxx:22
. 2018-06-27 10:36:12.206 --------------------------------------------------------------------------
. 2018-06-27 10:36:12.221 Connecting via tunnel interface 127.0.0.1:50022.
. 2018-06-27 10:36:12.237 Looking up host "127.0.0.1" for SSH connection
. 2018-06-27 10:36:12.237 Connecting to 127.0.0.1 port 50022
. 2018-06-27 10:36:12.237 We claim version: SSH-2.0-WinSCP_release_5.13.1
. 2018-06-27 10:36:12.237 [Tunnel] Opening connection to xxx.xxx.xxx.xxx:22 for forwarding from 127.0.0.1:50553
. 2018-06-27 10:36:12.251 [Tunnel] Forwarded connection refused by server: Connect failed []
. 2018-06-27 10:36:12.503 [Tunnel] Closing connection.
. 2018-06-27 10:36:12.503 [Tunnel] Sending special code: 12
. 2018-06-27 10:36:12.503 [Tunnel] Sent EOF message
. 2018-06-27 10:36:12.503 Network error: Software caused connection abort
* 2018-06-27 10:36:12.520 (EFatal) Network error: Software caused connection abort
* 2018-06-27 10:36:12.520 Error while tunneling the connection.
* 2018-06-27 10:36:12.520
* 2018-06-27 10:36:12.520 Connect failed ().
. 2018-06-26 15:10:56.442 --------------------------------------------------------------------------
. 2018-06-26 15:10:56.442 WinSCP Version 5.13.1 (Build 8265) (OS 6.3.9600 - Windows Server 2012 R2 Standard)
. 2018-06-26 15:10:56.442 Configuration: HKCU\Software\Martin Prikryl\WinSCP 2\
. 2018-06-26 15:10:56.443 Log level: Normal, Logging passwords
. 2018-06-26 15:10:56.443 Local account: IP-AC1F0391\xxxXXxxx
. 2018-06-26 15:10:56.443 Working directory: C:\Program Files (x86)\WinSCP
. 2018-06-26 15:10:56.443 Process ID: 10376
. 2018-06-26 15:10:56.443 Command-line: "C:\Program Files (x86)\WinSCP\WinSCP.exe"
. 2018-06-26 15:10:56.443 Time zone: Current: GMT+1, Standard: GMT+0 (GMT Standard Time), DST: GMT+1 (GMT Summer Time), DST Start: 25/03/2018, DST End: 28/10/2018
. 2018-06-26 15:10:56.443 Login time: 26 June 2018 15:10:56
. 2018-06-26 15:10:56.443 --------------------------------------------------------------------------
. 2018-06-26 15:10:56.443 Session name: XXXXX (Site)
. 2018-06-26 15:10:56.443 Host name: xxx.xxx.xxx.xxx (Port: 22)
. 2018-06-26 15:10:56.443 User name: XXXxxXXX (Password: No, Key file: No, Passphrase: No)
. 2018-06-26 15:10:56.443 Tunnel: Yes
. 2018-06-26 15:10:56.443 Tunnel: Host name: xxx.xxx.xxx.xxx (Port: 22)
. 2018-06-26 15:10:56.443 Tunnel: User name: XXXxxXXX (Password: No, Key file: C:\Users\xxxXXxxx\Desktop\XXXxxXXX.ppk)
. 2018-06-26 15:10:56.443 Tunnel: Local port number: 0
. 2018-06-26 15:10:56.443 Transfer Protocol: SFTP (SCP)
. 2018-06-26 15:10:56.443 Ping type: Off, Ping interval: 30 sec; Timeout: 15 sec
. 2018-06-26 15:10:56.443 Disable Nagle: No
. 2018-06-26 15:10:56.443 Proxy: None
. 2018-06-26 15:10:56.443 Send buffer: 262144
. 2018-06-26 15:10:56.443 SSH protocol version: 2; Compression: No
. 2018-06-26 15:10:56.443 Bypass authentication: No
. 2018-06-26 15:10:56.443 Try agent: Yes; Agent forwarding: No; TIS/CryptoCard: No; KI: Yes; GSSAPI: Yes
. 2018-06-26 15:10:56.443 GSSAPI: Forwarding: No; Libs: gssapi32,sspi,custom; Custom:
. 2018-06-26 15:10:56.443 Ciphers: aes,chacha20,blowfish,3des,WARN,arcfour,des; Ssh2DES: No
. 2018-06-26 15:10:56.443 KEX: ecdh,dh-gex-sha1,dh-group14-sha1,rsa,WARN,dh-group1-sha1
. 2018-06-26 15:10:56.443 SSH Bugs: Auto,Auto,Auto,Auto,Auto,Auto,Auto,Auto,Auto,Auto,Auto,Auto,Auto
. 2018-06-26 15:10:56.443 Simple channel: Yes
. 2018-06-26 15:10:56.443 Return code variable: Autodetect; Lookup user groups: Auto
. 2018-06-26 15:10:56.443 Shell: default
. 2018-06-26 15:10:56.443 EOL: LF, UTF: Auto
. 2018-06-26 15:10:56.443 Clear aliases: Yes, Unset nat.vars: Yes, Resolve symlinks: Yes; Follow directory symlinks: No
. 2018-06-26 15:10:56.443 LS: ls -la, Ign LS warn: Yes, Scp1 Comp: No
. 2018-06-26 15:10:56.443 SFTP Bugs: Auto,Auto
. 2018-06-26 15:10:56.443 SFTP Server: default
. 2018-06-26 15:10:56.443 Local directory: default, Remote directory: home, Update: Yes, Cache: Yes
. 2018-06-26 15:10:56.443 Cache directory changes: Yes, Permanent: Yes
. 2018-06-26 15:10:56.443 Recycle bin: Delete to: No, Overwritten to: No, Bin path:
. 2018-06-26 15:10:56.443 DST mode: Unix
. 2018-06-26 15:10:56.443 --------------------------------------------------------------------------
. 2018-06-26 15:10:56.478 Opening tunnel.
. 2018-06-26 15:10:56.478 Autoselected tunnel local port number 50000
. 2018-06-26 15:10:56.501 [Tunnel] Looking up host "xxx.xxx.xxx.xxx" for SSH connection
. 2018-06-26 15:10:56.501 [Tunnel] Connecting to xxx.xxx.xxx.xxx port 22
. 2018-06-26 15:10:56.513 [Tunnel] We claim version: SSH-2.0-WinSCP_release_5.13.1
. 2018-06-26 15:10:56.536 [Tunnel] Server version: SSH-2.0-WeOnlyDo 2.4.3
. 2018-06-26 15:10:56.536 [Tunnel] Using SSH protocol version 2
. 2018-06-26 15:10:56.536 [Tunnel] Have a known host key of type dss
. 2018-06-26 15:10:56.548 [Tunnel] Doing ECDH key exchange with curve nistp256 and hash SHA-256
. 2018-06-26 15:10:56.637 [Tunnel] Host key fingerprint is:
. 2018-06-26 15:10:56.637 [Tunnel] ssh-dss 1024 87:ae:5f:c9:4c:02:96:b1:04:dd:b0:04:31:6b:9d:27 kwLs2HHyixqdVyriERMs+g/mW7VlEn1S4NOG4MTZ+xo=
. 2018-06-26 15:10:56.642 [Tunnel] Host key matches cached key
. 2018-06-26 15:10:56.642 [Tunnel] Initialised AES-256 SDCTR client->server encryption
. 2018-06-26 15:10:56.642 [Tunnel] Initialised HMAC-SHA-256 client->server MAC algorithm
. 2018-06-26 15:10:56.654 [Tunnel] Initialised AES-256 SDCTR server->client encryption
. 2018-06-26 15:10:56.654 [Tunnel] Initialised HMAC-SHA-256 server->client MAC algorithm
. 2018-06-26 15:10:56.666 [Tunnel] Reading key file "C:\Users\xxxXXxxx\Desktop\XXXxxXXX.ppk"
. 2018-06-26 15:10:56.666 [Tunnel] Pageant is running. Requesting keys.
. 2018-06-26 15:10:56.667 [Tunnel] Pageant has 0 SSH-2 keys
. 2018-06-26 15:10:56.667 [Tunnel] Configured key file not in Pageant
! 2018-06-26 15:10:56.667 [Tunnel] Using username "XXXxxXXX".
. 2018-06-26 15:10:56.688 [Tunnel] Server offered these authentication methods: publickey
. 2018-06-26 15:10:56.688 [Tunnel] Offered public key
. 2018-06-26 15:10:56.711 [Tunnel] Offer of public key accepted
! 2018-06-26 15:10:56.711 [Tunnel] Authenticating with public key "XXXxxXXX"
. 2018-06-26 15:10:56.849 [Tunnel] Sent public key signature
. 2018-06-26 15:10:56.863 [Tunnel] Access granted
. 2018-06-26 15:10:56.863 [Tunnel] Local port 50000 forwarding to xxx.xxx.xxx.xxx:22
. 2018-06-26 15:10:56.898 --------------------------------------------------------------------------
. 2018-06-26 15:10:56.912 Connecting via tunnel interface 127.0.0.1:50000.
. 2018-06-26 15:10:56.926 Looking up host "127.0.0.1" for SSH connection
. 2018-06-26 15:10:56.926 Connecting to 127.0.0.1 port 50000
. 2018-06-26 15:10:56.927 We claim version: SSH-2.0-WinSCP_release_5.13.1
. 2018-06-26 15:10:56.927 [Tunnel] Opening connection to xxx.xxx.xxx.xxx:22 for forwarding from 127.0.0.1:54541
. 2018-06-26 15:10:56.939 [Tunnel] Forwarded connection refused by server: Connect failed []
. 2018-06-26 15:10:57.191 [Tunnel] Closing connection.
. 2018-06-26 15:10:57.191 [Tunnel] Sending special code: 12
. 2018-06-26 15:10:57.191 [Tunnel] Sent EOF message
. 2018-06-26 15:10:57.191 Network error: Software caused connection abort
* 2018-06-26 15:10:57.208 (EFatal) Network error: Software caused connection abort
* 2018-06-26 15:10:57.208 Error while tunneling the connection.
* 2018-06-26 15:10:57.208
* 2018-06-26 15:10:57.208 Connect failed ().