Ansible on Windows with Plink and shared connection

ansible.cfg

[defaults]
inventory = inventory.ini
host_key_checking = False

[ssh_connection]
ssh_executable = ./plink-wrapper.sh
transfer_method = piped

plink-wrapper.sh

#!/bin/bash
# plink-wrapper.sh

PLINK="plink.exe"
HOST=""
CMD=""

# Parse args - skip all OpenSSH options
while [[ $# -gt 0 ]]; do
    case "$1" in
        -o) shift ;;           # Skip -o and its value
        -C|-T|-q|-a|-x|-n) ;;  # Skip single flags
        -p|-l|-i) shift ;;     # Skip flag + value
        -*)  ;;                # Skip unknown flags
        *)  
            if [[ -z "$HOST" ]]; then
                HOST="$1"
            else
                CMD="$*"
                break
            fi
            ;;
    esac
    shift
done

# No -t flag! It breaks piped transfers
exec $PLINK -load "$HOST" -batch -share "$CMD"

ssh_to_putty.py

#!/usr/bin/env python3
"""Import OpenSSH config hosts into PuTTY sessions."""

import re
import os
import winreg
from pathlib import Path
from urllib.parse import quote

def parse_ssh_config(config_path=None):
    """Parse ~/.ssh/config and return list of host configurations."""
    if config_path is None:
        config_path = Path.home() / ".ssh" / "config"
    
    hosts = []
    current_host = None
    
    with open(config_path, 'r') as f:
        for line in f:
            line = line.strip()
            if not line or line.startswith('#'):
                continue
            
            match = re.match(r'^(\S+)\s+(.+)$', line)
            if not match:
                continue
                
            key, value = match.groups()
            key = key.lower()
            
            if key == 'host':
                if current_host and '*' not in current_host.get('host', ''):
                    hosts.append(current_host)
                current_host = {'host': value}
            elif current_host:
                current_host[key] = value
        
        # Don't forget the last host
        if current_host and '*' not in current_host.get('host', ''):
            hosts.append(current_host)
    
    return hosts

def create_putty_session(host_config, dry_run=False):
    """Create a PuTTY session in the registry."""
    session_name = host_config['host']
    # PuTTY URL-encodes session names
    session_key = quote(session_name, safe='')
    
    reg_path = rf"Software\SimonTatham\PuTTY\Sessions\{session_key}"
    
    # Map SSH config to PuTTY registry values
    values = {}
    
    # HostName
    if 'hostname' in host_config:
        values['HostName'] = host_config['hostname']
    else:
        values['HostName'] = host_config['host']
    
    # User
    if 'user' in host_config:
        values['UserName'] = host_config['user']
    
    # Port
    if 'port' in host_config:
        values['PortNumber'] = int(host_config['port'])
    
    # IdentityFile (convert to Windows path and PuTTY format)
    if 'identityfile' in host_config:
        key_path = host_config['identityfile']
        key_path = os.path.expanduser(key_path)
        # Convert to .ppk if needed (PuTTY uses different key format)
        values['PublicKeyFile'] = key_path.replace('/', '\\')
    
    # ProxyJump -> PuTTY proxy command
    if 'proxyjump' in host_config:
        values['ProxyMethod'] = 6  # Local proxy command
        proxy_host = host_config['proxyjump']
        values['ProxyTelnetCommand'] = f'plink -batch -share {proxy_host} -nc %host:%port'
    
    # Connection sharing
    values['ConnectionSharing'] = 1
    values['ConnectionSharingUpstream'] = 1
    values['ConnectionSharingDownstream'] = 1
    
    if dry_run:
        print(f"\n[Session: {session_name}]")
        for k, v in values.items():
            print(f"  {k} = {v}")
        return
    
    # Write to registry
    try:
        key = winreg.CreateKey(winreg.HKEY_CURRENT_USER, reg_path)
        for name, value in values.items():
            if isinstance(value, int):
                winreg.SetValueEx(key, name, 0, winreg.REG_DWORD, value)
            else:
                winreg.SetValueEx(key, name, 0, winreg.REG_SZ, str(value))
        winreg.CloseKey(key)
        print(f"Created session: {session_name}")
    except Exception as e:
        print(f"Error creating {session_name}: {e}")

def main():
    import argparse
    parser = argparse.ArgumentParser(description='Import SSH config to PuTTY')
    parser.add_argument('--config', '-c', help='Path to SSH config file')
    parser.add_argument('--dry-run', '-n', action='store_true', 
                        help='Show what would be created without writing to registry')
    args = parser.parse_args()
    
    hosts = parse_ssh_config(args.config)
    print(f"Found {len(hosts)} hosts in SSH config")
    
    for host in hosts:
        create_putty_session(host, dry_run=args.dry_run)
    
    if not args.dry_run:
        print("\nDone! Restart PuTTY to see the new sessions.")
        print("Note: If you use SSH keys, convert them to .ppk format with PuTTYgen")

if __name__ == '__main__':
    main()