🪟Plink Windows Pivoting

📋 Module Overview

Purpose: Windows-based SSH tunneling and pivoting using Plink.exe Tool: PuTTY Link (plink.exe) - Windows command-line SSH client Scenario: Windows attack host or compromised Windows pivot Technique: Dynamic port forwarding with SOCKS proxy Integration: Proxifier for Windows application tunneling

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1. Introduction to Plink.exe

What is Plink?

• Full Name: PuTTY Link

• Type: Windows command-line SSH tool

• Package: Part of PuTTY suite

• Capability: SSH tunneling, port forwarding, SOCKS proxy

• Era: Pre-Windows 10 standard (before native OpenSSH)

Why Use Plink?

1. Living off the Land - often pre-installed on Windows systems

2. Windows Native - no need to transfer additional tools

3. Stealth - uses legitimate administrative tool

4. Compatibility - works on older Windows versions

5. Integration - pairs well with Windows tools like Proxifier

Common Scenarios

• Windows-based attack host instead of Linux

• Compromised Windows system as pivot point

• Locked down environment where uploading tools is risky

• Legacy systems with PuTTY already installed

• File share access to plink.exe without installation

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2. Plink vs SSH Comparison

Aspect	SSH (Linux)	Plink (Windows)
Platform	Linux/Unix	Windows
Syntax	ssh -D 9050 user@host	plink -ssh -D 9050 user@host
Authentication	Key/password	Key/password
Integration	Native Linux tools	Proxifier, Windows apps
Stealth	Standard on Linux	Legitimate Windows tool
Availability	Always present	Depends on PuTTY install

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3. Basic Plink Dynamic Port Forwarding

Network Topology

[Windows Attack Host] → [Ubuntu Pivot] → [Internal Network]
    10.10.15.5           10.129.15.50      172.16.5.0/24
    Plink Client         SSH Server        Target Systems
    SOCKS :9050

Command Syntax

# Basic dynamic port forward with Plink
plink -ssh -D 9050 ubuntu@10.129.15.50

# Command breakdown:
# -ssh        - Use SSH protocol
# -D 9050     - Dynamic port forward on local port 9050
# ubuntu      - Username on pivot host
# @10.129.15.50 - Pivot host IP address

Expected Output

Using username "ubuntu".
ubuntu@10.129.15.50's password:
Welcome to Ubuntu 20.04.3 LTS (GNU/Linux 5.4.0-88-generic x86_64)

 * Documentation:  https://help.ubuntu.com
 * Management:     https://landscape.canonical.com
 * Support:        https://ubuntu.com/advantage

Last login: Mon Mar  7 15:30:45 2022 from 10.10.15.5
ubuntu@pivot:~$

Verification

# Check if SOCKS proxy is listening (Windows Command Prompt)
netstat -an | findstr :9050

# Expected output:
TCP    127.0.0.1:9050         0.0.0.0:0              LISTENING

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4. Proxifier Integration

What is Proxifier?

• Purpose: Windows SOCKS/HTTP proxy client

• Function: Routes application traffic through proxies

• Capability: Proxy chaining, application-specific routing

• Target: Desktop applications (RDP, browsers, etc.)

Proxifier Configuration Steps

Step 1: Add SOCKS Server

Proxifier → Profile Menu → Proxy Servers → Add

Server Configuration:
- Address: 127.0.0.1
- Port: 9050
- Protocol: SOCKS Version 4
- Authentication: None (for basic setup)

Step 2: Create Proxification Rules

Proxifier → Profile Menu → Proxification Rules → Add

Rule Configuration:
- Name: "RDP through Plink"
- Applications: mstsc.exe
- Target hosts: 172.16.5.*
- Action: Proxy SOCKS 127.0.0.1:9050

Step 3: Enable Proxification

Proxifier → Profile Menu → Proxification Rules → Enable Rules
Check: "Process all connections through proxy"

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5. RDP Through Plink SOCKS Tunnel

Complete Workflow

Step 1: Start Plink SOCKS Tunnel

# Windows Command Prompt
plink -ssh -D 9050 ubuntu@10.129.15.50

# Keep this session active for tunneling

Step 2: Configure Proxifier

1. Open Proxifier
2. Add SOCKS proxy: 127.0.0.1:9050
3. Create rule for mstsc.exe
4. Enable proxification

Step 3: Launch RDP Session

# Start Remote Desktop Connection
mstsc.exe

# Connect to internal target:
Computer: 172.16.5.19
Username: victor
Password: pass@123

Traffic Flow Analysis

[mstsc.exe] → [Proxifier] → [Plink SOCKS] → [SSH Tunnel] → [Ubuntu Pivot] → [Windows Target RDP]
Windows RDP     Proxy        Local :9050     Encrypted      SSH Server      172.16.5.19:3389
Client          Client                       Connection

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6. Advanced Plink Techniques

Authentication Methods

Password Authentication

# Interactive password prompt
plink -ssh -D 9050 ubuntu@10.129.15.50

# Scripted password (less secure)
echo password | plink -ssh -D 9050 ubuntu@10.129.15.50 -pw

Key-based Authentication

# Using PuTTY private key format (.ppk)
plink -ssh -D 9050 -i C:\keys\ubuntu.ppk ubuntu@10.129.15.50

# Convert OpenSSH key to PuTTY format with PuTTYgen if needed

Multiple Port Forwards

# Dynamic + Local port forwards
plink -ssh -D 9050 -L 8080:172.16.5.19:80 ubuntu@10.129.15.50

# Multiple local forwards
plink -ssh -L 3389:172.16.5.19:3389 -L 445:172.16.5.19:445 ubuntu@10.129.15.50

Background Process

# Run Plink in background (Windows)
start /B plink -ssh -D 9050 ubuntu@10.129.15.50

# Check running processes
tasklist | findstr plink

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7. Windows Application Integration

Applications That Work with SOCKS Proxies

Native SOCKS Support

✅ Web Browsers (Firefox, Chrome with proxy)
✅ FTP Clients (WinSCP, FileZilla)
✅ SSH Clients (PuTTY, KiTTY)
✅ Tor Browser (built-in SOCKS)

Proxifier-Required Applications

⚙️ mstsc.exe (Remote Desktop)
⚙️ Windows Explorer (SMB shares)
⚙️ Command line tools (ping, telnet)
⚙️ Custom applications

Browser Configuration Example

Firefox → Settings → Network Settings → Manual Proxy Configuration
SOCKS Host: 127.0.0.1
Port: 9050
SOCKS v4

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8. Operational Security with Plink

Stealth Considerations

1. Legitimate Tool - Plink is standard administrative software

2. Network Noise - SSH traffic appears normal

3. Process Name - plink.exe is not suspicious

4. Registry Traces - Minimal system footprint

Detection Risks

1. Network Monitoring - SSH connections to pivot hosts

2. Process Monitoring - Unusual plink.exe usage patterns

3. Proxy Detection - SOCKS traffic analysis

4. Authentication Logs - SSH login records

Mitigation Strategies

# Use legitimate-looking SSH sessions
plink -ssh -D 9050 [e-mail]

# Vary timing and ports
plink -ssh -D 8080 ubuntu@10.129.15.50

# Clean up processes when done
taskkill /F /IM plink.exe

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9. Troubleshooting Plink Issues

Common Problems and Solutions

Authentication Failures

# Problem: Access denied
plink: Access denied

# Solutions:
1. Verify username/password
2. Check SSH key permissions
3. Confirm SSH service is running
4. Test with PuTTY GUI first

Connection Refused

# Problem: Network unreachable
plink: Network error: Connection refused

# Solutions:
1. Verify pivot host IP
2. Check SSH port (default 22)
3. Confirm firewall rules
4. Test with telnet

SOCKS Proxy Not Working

# Problem: Applications can't connect through proxy
# Solutions:
1. Verify port 9050 is listening
   netstat -an | findstr :9050

2. Check Proxifier configuration
3. Test with SOCKS-aware application
4. Restart Plink session

Proxifier Issues

# Problem: Proxifier not routing traffic
# Solutions:
1. Check proxy server settings (127.0.0.1:9050)
2. Verify proxification rules
3. Enable debug logging
4. Restart Proxifier service

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10. Alternative Windows SSH Tools

Built-in Windows SSH (Windows 10+)

# Modern Windows has native SSH client
ssh -D 9050 ubuntu@10.129.15.50

# Check if available:
where ssh

Other Windows SSH Clients

# KiTTY (PuTTY fork)
kitty -ssh -D 9050 ubuntu@10.129.15.50

# Bitvise SSH Client
BvSsh -host=10.129.15.50 -user=ubuntu -localFwd=9050:127.0.0.1:9050

# MobaXterm
MobaXterm with SSH tunneling

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11. Lab Exercise Recreation

HTB Academy Optional Exercise

Task: "Attempt to use Plink from a Windows-based attack host. Set up a proxy connection and RDP to the Windows target (172.16.5.19) with 'victor:pass@123'"

Complete Solution Steps

Step 1: Environment Setup

# Requirements:
- Windows attack host
- Plink.exe available
- Network access to 10.129.202.64 (pivot)
- Target: 172.16.5.19 (internal Windows)

Step 2: Establish Plink Tunnel

# Create SOCKS tunnel through Ubuntu pivot
plink -ssh -D 9050 ubuntu@10.129.202.64

# Enter password when prompted
ubuntu@10.129.202.64's password: HTB_@cademy_stdnt!

Step 3: Configure Proxifier

1. Open Proxifier
2. Profile → Proxy Servers → Add
   - Address: 127.0.0.1
   - Port: 9050
   - Type: SOCKS4
3. Profile → Proxification Rules → Add
   - Applications: mstsc.exe
   - Target Hosts: 172.16.5.19
   - Action: Proxy 127.0.0.1:9050

Step 4: RDP Connection

# Launch Remote Desktop
mstsc.exe

# Connection details:
Computer: 172.16.5.19
User name: victor
Password: pass@123

Step 5: Submit Answer

Answer: "I tried Plink"

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12. Comparison with Linux SSH Methods

Functionality Comparison

Feature	Linux SSH	Windows Plink
Dynamic Forward	ssh -D 9050	plink -ssh -D 9050
Local Forward	ssh -L 8080:target:80	plink -ssh -L 8080:target:80
Remote Forward	ssh -R 8080:localhost:80	plink -ssh -R 8080:localhost:80
Background	ssh -fN -D 9050	start /B plink -ssh -D 9050
Key Auth	ssh -i key	plink -i key.ppk

Integration Differences

Linux Integration

# Direct proxychains support
proxychains nmap -sT 172.16.5.19

# Built-in SOCKS applications
curl --socks5 127.0.0.1:9050 http://172.16.5.19

Windows Integration

# Requires Proxifier for most applications
Proxifier → mstsc.exe → 172.16.5.19

# Some native SOCKS support
firefox → proxy settings → SOCKS 127.0.0.1:9050

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13. Real-World Scenarios

Scenario 1: Corporate Windows Environment

Situation: Pentesting corporate network
Environment: Windows workstations with PuTTY installed
Goal: Pivot through DMZ host to internal network
Solution: Use Plink for SOCKS tunneling + Proxifier for RDP

Scenario 2: Legacy System Compromise

Situation: Compromised older Windows server
Limitation: Cannot upload new tools
Available: PuTTY suite installed for administration
Solution: Leverage existing Plink for tunneling

Scenario 3: Windows Red Team Operation

Situation: Windows-based red team infrastructure
Challenge: Need to blend in with Windows environment
Approach: Use Windows-native tools (Plink, Proxifier, mstsc)
Benefit: Reduced detection, natural tool usage

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14. Best Practices

Operational Guidelines

1. Test Locally First - Verify Plink works before deployment

2. Multiple Tunnels - Create redundant paths when possible

3. Authentication Security - Use keys when possible

4. Clean Exit - Properly terminate sessions

5. Documentation - Record tunnel configurations

Security Recommendations

1. Timing Variation - Don't establish tunnels at predictable times

2. Port Diversity - Use different SOCKS ports

3. Session Management - Monitor and limit session duration

4. Log Cleanup - Clear relevant Windows event logs

5. Process Hiding - Consider process migration techniques

Performance Optimization

1. Compression - Use SSH compression for slow links

2. Keep-Alive - Maintain persistent connections

3. Concurrent Sessions - Balance load across multiple tunnels

4. Bandwidth Monitoring - Track usage patterns

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15. Integration with Other Tools

Metasploit Integration

# Metasploit with SOCKS proxy (requires Proxychains4Windows)
msf6 > setg Proxies socks4:127.0.0.1:9050
msf6 > use auxiliary/scanner/portscan/tcp
msf6 auxiliary(scanner/portscan/tcp) > set RHOSTS 172.16.5.19
msf6 auxiliary(scanner/portscan/tcp) > run

PowerShell Integration

# PowerShell with proxy settings
$proxy = New-Object System.Net.WebProxy("socks://127.0.0.1:9050")
$webClient = New-Object System.Net.WebClient
$webClient.Proxy = $proxy
$webClient.DownloadString("http://172.16.5.19")

Nmap through Proxy

# Using ProxyChains4Windows (if available)
proxychains4 nmap -sT -Pn 172.16.5.19

# Alternative: nmap with HTTP proxy (if SOCKS-to-HTTP converter used)
nmap --proxy socks4://127.0.0.1:9050 172.16.5.19

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References

• HTB Academy: Pivoting, Tunneling & Port Forwarding - Page 8

• PuTTY Documentation: Official PuTTY Manual

• Proxifier Manual: Proxifier Documentation

• SANS: SSH Tunneling with Windows

• Microsoft: Windows SSH Client