In this scenario, I will demonstrate how I can get connectivity to the Domain Controller via a local Windows machine + access a KALI with VPN and finally the Domain Controller.
We have the following scenario in a red teaming assessment:
Windows local machine (e.g., CommandoVM) authenticated with VPN into the target infrastructure.
A kali machine is accessible through VPN on the target infrastructure. This machine talks with the Domain Controller. We can use the Windows VM to execute programs and Powershell commands within the context of a domain user.
In sum, we can authenticate with the Windows VM into the Kali and forward all the traffic to the Domain Controller. Using an openvpn on the Kali, we can achieve this goal in a highly restricted environment.
Windows VM - Connecting via VPN
Install OpenVPN Kali Linux
After the installation, ensure that all the certificates were generated and are in place:
After generating all the files, the "ca.crt", "client.crt" and "client.key" must be zipped and copied into the Windows VM to add them to the ovpn config file as follows:
ca C:\\Users\\IEUser\\Desktop\\openvpn\\ca.crt
cert C:\\Users\\IEUser\\Desktop\\openvpn\\client.crt
key C:\\Users\\IEUser\\Desktop\\openvpn\\client.key
Windows OpenVPN
Install the OpenVPN. Before connecting ensure that:
Connection to the target environment was achieved (Windows VM Connecting via VPN above)
Create an SSH tunnel on port: 1194 from the Kali machine available on the internal network
ssh -L1194:127.0.0.1:1194 username@target_kali
Configurations Kali
On the kali through SSH connection above ensure that IP tables are in place, e.g.:
This command configures network address translation (NAT) using iptables, a utility for configuring the Linux kernel's firewall. Let's break down the command:
iptables: This is the command-line utility used to configure the Linux kernel's firewall.
-t nat: This option specifies the table within iptables that we are working with. In this case, it's the NAT table, which is responsible for Network Address Translation.
-A POSTROUTING: This option appends a rule to the end of the POSTROUTING chain. This chain is used for packets that are about to be sent out of the system.
-s 10.8.0.0/24: This specifies the source IP addresses that match the rule. Here, it's set to the subnet 10.8.0.0/24, meaning all IP addresses from 10.8.0.1 to 10.8.0.254.
-o eth0: This specifies the outgoing network interface. In this case, it's eth0, which is a common network interface name on Linux systems.
-j MASQUERADE: This is the action to take if the packet matches the rule. Here, it's set to MASQUERADE, which means that the source IP address of the packet will be replaced with the IP address of the outgoing interface (eth0). This is commonly used for NAT when sharing internet access with multiple devices in a private network.
and
net.ipv4.ip_forward: This kernel parameter determines whether the system forwards IPv4 packets between network interfaces. When set to 1, it enables IP forwarding, allowing the Linux system to act as a router, forwarding packets between different network interfaces.
Finally, start the openvpn server as follows:
sudo openvpn --config server.conf
Server config is something like this:
#################################################
# Sample OpenVPN 2.0 config file for #
# multi-client server. #
# #
# This file is for the server side #
# of a many-clients <-> one-server #
# OpenVPN configuration. #
# #
# OpenVPN also supports #
# single-machine <-> single-machine #
# configurations (See the Examples page #
# on the web site for more info). #
# #
# This config should work on Windows #
# or Linux/BSD systems. Remember on #
# Windows to quote pathnames and use #
# double backslashes, e.g.: #
# "C:\\Program Files\\OpenVPN\\config\\foo.key" #
# #
# Comments are preceded with '#' or ';' #
#################################################
# Which local IP address should OpenVPN
# listen on? (optional)
;local a.b.c.d
# Which TCP/UDP port should OpenVPN listen on?
# If you want to run multiple OpenVPN instances
# on the same machine, use a different port
# number for each one. You will need to
# open up this port on your firewall.
port 1194
# TCP or UDP server?
proto tcp
;proto udp
# "dev tun" will create a routed IP tunnel,
# "dev tap" will create an ethernet tunnel.
# Use "dev tap0" if you are ethernet bridging
# and have precreated a tap0 virtual interface
# and bridged it with your ethernet interface.
# If you want to control access policies
# over the VPN, you must create firewall
# rules for the the TUN/TAP interface.
# On non-Windows systems, you can give
# an explicit unit number, such as tun0.
# On Windows, use "dev-node" for this.
# On most systems, the VPN will not function
# unless you partially or fully disable
# the firewall for the TUN/TAP interface.
;dev tap
dev tun
# Windows needs the TAP-Win32 adapter name
# from the Network Connections panel if you
# have more than one. On XP SP2 or higher,
# you may need to selectively disable the
# Windows firewall for the TAP adapter.
# Non-Windows systems usually don't need this.
;dev-node MyTap
# SSL/TLS root certificate (ca), certificate
# (cert), and private key (key). Each client
# and the server must have their own cert and
# key file. The server and all clients will
# use the same ca file.
#
# See the "easy-rsa" directory for a series
# of scripts for generating RSA certificates
# and private keys. Remember to use
# a unique Common Name for the server
# and each of the client certificates.
#
# Any X509 key management system can be used.
# OpenVPN can also use a PKCS #12 formatted key file
# (see "pkcs12" directive in man page).
ca ca.crt
cert server.crt
key server.key # This file should be kept secret
# Diffie hellman parameters.
# Generate your own with:
# openssl dhparam -out dh2048.pem 2048
dh dh2048.pem
# Network topology
# Should be subnet (addressing via IP)
# unless Windows clients v2.0.9 and lower have to
# be supported (then net30, i.e. a /30 per client)
# Defaults to net30 (not recommended)
;topology subnet
# Configure server mode and supply a VPN subnet
# for OpenVPN to draw client addresses from.
# The server will take 10.8.0.1 for itself,
# the rest will be made available to clients.
# Each client will be able to reach the server
# on 10.8.0.1. Comment this line out if you are
# ethernet bridging. See the man page for more info.
server 10.8.0.0 255.255.255.0
# Maintain a record of client <-> virtual IP address
# associations in this file. If OpenVPN goes down or
# is restarted, reconnecting clients can be assigned
# the same virtual IP address from the pool that was
# previously assigned.
ifconfig-pool-persist /var/log/openvpn/ipp.txt
# Configure server mode for ethernet bridging.
# You must first use your OS's bridging capability
# to bridge the TAP interface with the ethernet
# NIC interface. Then you must manually set the
# IP/netmask on the bridge interface, here we
# assume 10.8.0.4/255.255.255.0. Finally we
# must set aside an IP range in this subnet
# (start=10.8.0.50 end=10.8.0.100) to allocate
# to connecting clients. Leave this line commented
# out unless you are ethernet bridging.
;server-bridge 10.8.0.4 255.255.255.0 10.8.0.50 10.8.0.100
# Configure server mode for ethernet bridging
# using a DHCP-proxy, where clients talk
# to the OpenVPN server-side DHCP server
# to receive their IP address allocation
# and DNS server addresses. You must first use
# your OS's bridging capability to bridge the TAP
# interface with the ethernet NIC interface.
# Note: this mode only works on clients (such as
# Windows), where the client-side TAP adapter is
# bound to a DHCP client.
;server-bridge
# Push routes to the client to allow it
# to reach other private subnets behind
# the server. Remember that these
# private subnets will also need
# to know to route the OpenVPN client
# address pool (10.8.0.0/255.255.255.0)
# back to the OpenVPN server.
;push "route 192.168.10.0 255.255.255.0"
;push "route 192.168.20.0 255.255.255.0"
# To assign specific IP addresses to specific
# clients or if a connecting client has a private
# subnet behind it that should also have VPN access,
# use the subdirectory "ccd" for client-specific
# configuration files (see man page for more info).
# EXAMPLE: Suppose the client
# having the certificate common name "Thelonious"
# also has a small subnet behind his connecting
# machine, such as 192.168.40.128/255.255.255.248.
# First, uncomment out these lines:
;client-config-dir ccd
;route 192.168.40.128 255.255.255.248
# Then create a file ccd/Thelonious with this line:
# iroute 192.168.40.128 255.255.255.248
# This will allow Thelonious' private subnet to
# access the VPN. This example will only work
# if you are routing, not bridging, i.e. you are
# using "dev tun" and "server" directives.
# EXAMPLE: Suppose you want to give
# Thelonious a fixed VPN IP address of 10.9.0.1.
# First uncomment out these lines:
;client-config-dir ccd
;route 10.9.0.0 255.255.255.252
# Then add this line to ccd/Thelonious:
# ifconfig-push 10.9.0.1 10.9.0.2
# Suppose that you want to enable different
# firewall access policies for different groups
# of clients. There are two methods:
# (1) Run multiple OpenVPN daemons, one for each
# group, and firewall the TUN/TAP interface
# for each group/daemon appropriately.
# (2) (Advanced) Create a script to dynamically
# modify the firewall in response to access
# from different clients. See man
# page for more info on learn-address script.
;learn-address ./script
# If enabled, this directive will configure
# all clients to redirect their default
# network gateway through the VPN, causing
# all IP traffic such as web browsing and
# and DNS lookups to go through the VPN
# (The OpenVPN server machine may need to NAT
# or bridge the TUN/TAP interface to the internet
# in order for this to work properly).
push "redirect-gateway def1 bypass-dhcp"
# Certain Windows-specific network settings
# can be pushed to clients, such as DNS
# or WINS server addresses. CAVEAT:
# http://openvpn.net/faq.html#dhcpcaveats
# The addresses below refer to the public
# DNS servers provided by opendns.com.
;push "dhcp-option DNS 208.67.222.222"
;push "dhcp-option DNS 208.67.220.220"
# Uncomment this directive to allow different
# clients to be able to "see" each other.
# By default, clients will only see the server.
# To force clients to only see the server, you
# will also need to appropriately firewall the
# server's TUN/TAP interface.
;client-to-client
# Uncomment this directive if multiple clients
# might connect with the same certificate/key
# files or common names. This is recommended
# only for testing purposes. For production use,
# each client should have its own certificate/key
# pair.
#
# IF YOU HAVE NOT GENERATED INDIVIDUAL
# CERTIFICATE/KEY PAIRS FOR EACH CLIENT,
# EACH HAVING ITS OWN UNIQUE "COMMON NAME",
# UNCOMMENT THIS LINE OUT.
;duplicate-cn
# The keepalive directive causes ping-like
# messages to be sent back and forth over
# the link so that each side knows when
# the other side has gone down.
# Ping every 10 seconds, assume that remote
# peer is down if no ping received during
# a 120 second time period.
keepalive 10 120
# For extra security beyond that provided
# by SSL/TLS, create an "HMAC firewall"
# to help block DoS attacks and UDP port flooding.
#
# Generate with:
# openvpn --genkey --secret ta.key
#
# The server and each client must have
# a copy of this key.
# The second parameter should be '0'
# on the server and '1' on the clients.
;tls-auth ta.key 0 # This file is secret
tls-server
# Select a cryptographic cipher.
# This config item must be copied to
# the client config file as well.
# Note that v2.4 client/server will automatically
# negotiate AES-256-GCM in TLS mode.
# See also the ncp-cipher option in the manpage
cipher AES-256-CBC
# Enable compression on the VPN link and push the
# option to the client (v2.4+ only, for earlier
# versions see below)
;compress lz4-v2
;push "compress lz4-v2"
# For compression compatible with older clients use comp-lzo
# If you enable it here, you must also
# enable it in the client config file.
;comp-lzo
# The maximum number of concurrently connected
# clients we want to allow.
;max-clients 100
# It's a good idea to reduce the OpenVPN
# daemon's privileges after initialization.
#
# You can uncomment this out on
# non-Windows systems.
;user nobody
;group nogroup
# The persist options will try to avoid
# accessing certain resources on restart
# that may no longer be accessible because
# of the privilege downgrade.
persist-key
persist-tun
# Output a short status file showing
# current connections, truncated
# and rewritten every minute.
status /var/log/openvpn/openvpn-status.log
# By default, log messages will go to the syslog (or
# on Windows, if running as a service, they will go to
# the "\Program Files\OpenVPN\log" directory).
# Use log or log-append to override this default.
# "log" will truncate the log file on OpenVPN startup,
# while "log-append" will append to it. Use one
# or the other (but not both).
;log /var/log/openvpn/openvpn.log
;log-append /var/log/openvpn/openvpn.log
# Set the appropriate level of log
# file verbosity.
#
# 0 is silent, except for fatal errors
# 4 is reasonable for general usage
# 5 and 6 can help to debug connection problems
# 9 is extremely verbose
verb 3
# Silence repeating messages. At most 20
# sequential messages of the same message
# category will be output to the log.
;mute 20
# Notify the client that when the server restarts so it
# can automatically reconnect.
;explicit-exit-notify 1
Connecting OpenVPN Windows
ovpn file can be imported into the OpenVPN client by doing: Import > Import File > (select file)
##############################################
# Sample client-side OpenVPN 2.0 config file #
# for connecting to multi-client server. #
# #
# This configuration can be used by multiple #
# clients, however each client should have #
# its own cert and key files. #
# #
# On Windows, you might want to rename this #
# file so it has a .ovpn extension #
##############################################
# Specify that we are a client and that we
# will be pulling certain config file directives
# from the server.
client
# Use the same setting as you are using on
# the server.
# On most systems, the VPN will not function
# unless you partially or fully disable
# the firewall for the TUN/TAP interface.
;dev tap
dev tun
# Windows needs the TAP-Win32 adapter name
# from the Network Connections panel
# if you have more than one. On XP SP2,
# you may need to disable the firewall
# for the TAP adapter.
;dev-node MyTap
# Are we connecting to a TCP or
# UDP server? Use the same setting as
# on the server.
proto tcp
;proto udp
# The hostname/IP and port of the server.
# You can have multiple remote entries
# to load balance between the servers.
remote 127.0.0.1 1194
;remote my-server-2 1194
# Choose a random host from the remote
# list for load-balancing. Otherwise
# try hosts in the order specified.
;remote-random
# Keep trying indefinitely to resolve the
# host name of the OpenVPN server. Very useful
# on machines which are not permanently connected
# to the internet such as laptops.
resolv-retry infinite
# Most clients don't need to bind to
# a specific local port number.
nobind
# Downgrade privileges after initialization (non-Windows only)
;user nobody
;group nogroup
# Try to preserve some state across restarts.
persist-key
persist-tun
# If you are connecting through an
# HTTP proxy to reach the actual OpenVPN
# server, put the proxy server/IP and
# port number here. See the man page
# if your proxy server requires
# authentication.
;http-proxy-retry # retry on connection failures
;http-proxy [proxy server] [proxy port #]
# Wireless networks often produce a lot
# of duplicate packets. Set this flag
# to silence duplicate packet warnings.
;mute-replay-warnings
# SSL/TLS parms.
# See the server config file for more
# description. It's best to use
# a separate .crt/.key file pair
# for each client. A single ca
# file can be used for all clients.
ca C:\\Users\\IEUser\\Desktop\\openvpn\\ca.crt
cert C:\\Users\\IEUser\\Desktop\\openvpn\\client.crt
key C:\\Users\\IEUser\\Desktop\\openvpn\\client.key
# Verify server certificate by checking that the
# certicate has the correct key usage set.
# This is an important precaution to protect against
# a potential attack discussed here:
# http://openvpn.net/howto.html#mitm
#
# To use this feature, you will need to generate
# your server certificates with the keyUsage set to
# digitalSignature, keyEncipherment
# and the extendedKeyUsage to
# serverAuth
# EasyRSA can do this for you.
;remote-cert-tls server
# If a tls-auth key is used on the server
# then every client must also have the key.
;tls-auth ta.key 1
tls-client
# Select a cryptographic cipher.
# If the cipher option is used on the server
# then you must also specify it here.
# Note that v2.4 client/server will automatically
# negotiate AES-256-GCM in TLS mode.
# See also the ncp-cipher option in the manpage
cipher AES-256-CBC
# Enable compression on the VPN link.
# Don't enable this unless it is also
# enabled in the server config file.
#comp-lzo
# Set log file verbosity.
verb 3
# Silence repeating messages
;mute 20
and ... gotcha!
Test Connection
nslookup domain.local
If we can't reach it, we need to adjust probably the Windows routes to connect with the Domain Controller:
