PowerShell / PowerShell/Win32-OpenSSH

ProxyJump not working on `OpenSSH_for_Windows_9.5p1, LibreSSL 3.8.2`

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Description

Prerequisites
  • Write a descriptive title.
  • Make sure you are able to repro it on the latest version
  • Search the existing issues.
Steps to reproduce
  1. download v9.5.0.0p1-Beta/OpenSSH-Win64.zip
  2. run on pwsh.exe: .\OpenSSH-Win64-9.5\ssh.exe -vvv -o UserKnownHostsFile=NUL target-host
  • cat ~/.ssh/config
Host target-host
  HostName ${target-host}
  User root
  Port 2222
  ProxyJump proxy-host

Host proxy-host
    HostName ${proxy-host}
    User root
    Port 2220
Expected behavior

On MacOS

Screenshot 2024-06-14 at 16 19 49
Actual behavior
PS C:\Users\valor\Desktop> .\OpenSSH-Win64-9.5\ssh.exe -vvv -o UserKnownHostsFile=NUL target-host
OpenSSH_for_Windows_9.5p1, LibreSSL 3.8.2
debug1: Reading configuration data C:\\Users\\valor/.ssh/config
debug1: C:\\Users\\valor/.ssh/config line 11: Applying options for target-host
debug3: Failed to open file:C:/ProgramData/ssh/ssh_config error:2
debug2: resolve_canonicalize: hostname ${target-host} is address
debug1: Setting implicit ProxyCommand from ProxyJump: "C:\\Users\\valor\\Desktop\\OpenSSH-Win64-9.5\\ssh.exe"  -vvv -W "[%h]:%p" proxy-host
debug1: Executing proxy command: exec "C:\\Users\\valor\\Desktop\\OpenSSH-Win64-9.5\\ssh.exe"  -vvv -W "[${target-host}]:2222" proxy-host
debug3: spawning "C:\\Users\\valor\\Desktop\\OpenSSH-Win64-9.5\\ssh.exe"  -vvv -W "[${target-host}]:2222" proxy-host as subprocess
debug3: w32_getpeername ERROR: not sock :2
debug3: Failed to open file:C:/Users/valor/.ssh/id_rsa error:2
debug3: Failed to open file:C:/Users/valor/.ssh/id_rsa.pub error:2
debug3: failed to open file:C:/Users/valor/.ssh/id_rsa error:2
debug1: identity file C:\\Users\\valor/.ssh/id_rsa type -1
debug3: Failed to open file:C:/Users/valor/.ssh/id_rsa-cert error:2
debug3: Failed to open file:C:/Users/valor/.ssh/id_rsa-cert.pub error:2
debug3: failed to open file:C:/Users/valor/.ssh/id_rsa-cert error:2
debug1: identity file C:\\Users\\valor/.ssh/id_rsa-cert type -1
debug3: Failed to open file:C:/Users/valor/.ssh/id_ecdsa error:2
debug3: Failed to open file:C:/Users/valor/.ssh/id_ecdsa.pub error:2
debug3: failed to open file:C:/Users/valor/.ssh/id_ecdsa error:2
debug1: identity file C:\\Users\\valor/.ssh/id_ecdsa type -1
debug3: Failed to open file:C:/Users/valor/.ssh/id_ecdsa-cert error:2
debug3: Failed to open file:C:/Users/valor/.ssh/id_ecdsa-cert.pub error:2
debug3: failed to open file:C:/Users/valor/.ssh/id_ecdsa-cert error:2
debug1: identity file C:\\Users\\valor/.ssh/id_ecdsa-cert type -1
debug3: Failed to open file:C:/Users/valor/.ssh/id_ecdsa_sk error:2
debug3: Failed to open file:C:/Users/valor/.ssh/id_ecdsa_sk.pub error:2
debug3: failed to open file:C:/Users/valor/.ssh/id_ecdsa_sk error:2
debug1: identity file C:\\Users\\valor/.ssh/id_ecdsa_sk type -1
debug3: Failed to open file:C:/Users/valor/.ssh/id_ecdsa_sk-cert error:2
debug3: Failed to open file:C:/Users/valor/.ssh/id_ecdsa_sk-cert.pub error:2
debug3: failed to open file:C:/Users/valor/.ssh/id_ecdsa_sk-cert error:2
debug1: identity file C:\\Users\\valor/.ssh/id_ecdsa_sk-cert type -1
debug1: identity file C:\\Users\\valor/.ssh/id_ed25519 type 3
debug3: Failed to open file:C:/Users/valor/.ssh/id_ed25519-cert error:2
debug3: Failed to open file:C:/Users/valor/.ssh/id_ed25519-cert.pub error:2
debug3: failed to open file:C:/Users/valor/.ssh/id_ed25519-cert error:2
debug1: identity file C:\\Users\\valor/.ssh/id_ed25519-cert type -1
debug3: Failed to open file:C:/Users/valor/.ssh/id_ed25519_sk error:2
debug3: Failed to open file:C:/Users/valor/.ssh/id_ed25519_sk.pub error:2
debug3: failed to open file:C:/Users/valor/.ssh/id_ed25519_sk error:2
debug1: identity file C:\\Users\\valor/.ssh/id_ed25519_sk type -1
debug3: Failed to open file:C:/Users/valor/.ssh/id_ed25519_sk-cert error:2
debug3: Failed to open file:C:/Users/valor/.ssh/id_ed25519_sk-cert.pub error:2
debug3: failed to open file:C:/Users/valor/.ssh/id_ed25519_sk-cert error:2
OpenSSH_for_Windows_9.5p1, LibreSSL 3.8.2
debug1: identity file C:\\Users\\valor/.ssh/id_ed25519_sk-cert type -1
debug3: Failed to open file:C:/Users/valor/.ssh/id_xmss error:2
debug3: Failed to open file:C:/Users/valor/.ssh/id_xmss.pub error:2
debug3: failed to open file:C:/Users/valor/.ssh/id_xmss error:2
debug1: identity file C:\\Users\\valor/.ssh/id_xmss type -1
debug3: Failed to open file:C:/Users/valor/.ssh/id_xmss-cert error:2
debug1: Reading configuration data C:\\Users\\valor/.ssh/config
debug3: Failed to open file:C:/Users/valor/.ssh/id_xmss-cert.pub error:2
debug3: Failed to open file:C:/ProgramData/ssh/ssh_config error:2
debug3: failed to open file:C:/Users/valor/.ssh/id_xmss-cert error:2
debug1: identity file C:\\Users\\valor/.ssh/id_xmss-cert type -1
debug3: Failed to open file:C:/Users/valor/.ssh/id_dsa error:2
debug3: Failed to open file:C:/Users/valor/.ssh/id_dsa.pub error:2
debug3: failed to open file:C:/Users/valor/.ssh/id_dsa error:2
debug1: identity file C:\\Users\\valor/.ssh/id_dsa type -1
debug3: Failed to open file:C:/Users/valor/.ssh/id_dsa-cert error:2
debug3: Failed to open file:C:/Users/valor/.ssh/id_dsa-cert.pub error:2
debug3: failed to open file:C:/Users/valor/.ssh/id_dsa-cert error:2
debug1: identity file C:\\Users\\valor/.ssh/id_dsa-cert type -1
debug1: Local version string SSH-2.0-OpenSSH_for_Windows_9.5
debug3: expanded UserKnownHostsFile '~/.ssh/known_hosts' -> 'C:\\Users\\valor/.ssh/known_hosts'
debug3: expanded UserKnownHostsFile '~/.ssh/known_hosts2' -> 'C:\\Users\\valor/.ssh/known_hosts2'
debug2: resolving "proxy-host" port 22
debug3: resolve_host: lookup proxy-host:22
ssh: Could not resolve hostname proxy-host: \262\273\326\252\265\300\325\342\321\371\265\304\326\367\273\372\241\243 
kex_exchange_identification: Connection closed by remote host
Connection closed by UNKNOWN port 65535
Error details

No response

Environment data
> $PSVersionTable

Name                           Value
----                           -----
PSVersion                      7.4.2
PSEdition                      Core
GitCommitId                    7.4.2
OS                             Microsoft Windows 10.0.22635
Platform                       Win32NT
PSCompatibleVersions           {1.0, 2.0, 3.0, 4.0…}
PSRemotingProtocolVersion      2.3
SerializationVersion           1.1.0.1
WSManStackVersion              3.0
Version

OpenSSH_for_Windows_9.5p1, LibreSSL 3.8.2

Visuals

No response

Contributor guide

Open the contributing guide

First steps

  1. Read the whole issue, then the project's contributing guide.
  2. Comment on the issue to say you are picking it up — it saves two people doing the same work.
  3. Fork the repository and make your change on a branch.
  4. Open a pull request that references the issue number.

Research direction

Start with the PowerShell ssh.exe command and the ~/.ssh/config entries for target-host and proxy-host, then compare the verbose Windows trace with the stated macOS behavior. Reproduce the ProxyJump connection using OpenSSH_for_Windows_9.5p1 and determine why proxy-host resolution fails; done means target-host connects through proxy-host without the shown error.

Written by the indexing model from the issue text.

Assessment

Tech stack
c, powershell
Domain
networking, operating-systems
Issue type
Bug
Difficulty
4/5
Estimated time
3-5 days
Activity status
Stale
Clarity
Mostly clear
Newbie friendliness
35/100

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