Running Metasploitable3

metasploitable3.md

Overview

Metasploitable3 by rapid7 is an environment built for testing metapsploit. Unfortunately, it hasn't been updated in many years and the default instructions on their page are wrong.

This walkthrough is based on Ubuntu 22.04, so subject to change.

Official page here: https://github.com/rapid7/metasploitable3

Steps

Step 1 -- Vagrant

Install vagrant. Follow the instructions on their page for the most up-to-date details for your distro:

https://developer.hashicorp.com/vagrant/downloads

Step 2 -- VirtualBox

Ensure you have virtualbox installed. Virtualbox is on most distributions already. For example, installation on 22.04 is as easy as:

sudo apt-get install virtualbox

Step 3 -- Get vagrant file

Here we will follow the same instructions as metasploitable3 directly:

mkdir metasploitable3-workspace
cd metasploitable3-workspace
curl -O https://raw.githubusercontent.com/rapid7/metasploitable3/master/Vagrantfile

Step 4 -- Openssl config

Download the openssl.cnf posted along with this gist. This is important since, due to the age of metasploit and it's VMs, we need to enable older, unsafe, ciphers. Place it in the same directory as your Vagrantfile

Step 5 -- Install vagrant plugins

You likely will need to add plugins if you haven't normally been using vagrant. Do that as follows:

vagrant plugin install winrm
vagrant plugin install winrm-fs
vagrant plugin install winrm-elevated

Step 6 -- Start up the metasploitable3 VM

We're now ready to start the VM. Do it with the following command:

OPENSSL_CONF=$PWD/openssl.cnf MS3_DIFFICULTY=easy vagrant up --provider=virtualbox win2k8

This will cause vagrant to download the VM and run it. Parameters I'm using:

• OPENSSL_CONF -- this is required to allow openssl/winrm to connect properly
• MS3_DIFFICULTY -- Optional, this just tells metasploitable3 to open up the firewall
• --provider=virtualbox -- As of writing, the default Vagrantfile is broken as it tells vagrant to use libvirt box, but they never pushed libvirt so it won't work. This forces vagrant to use virtualbox instead. NOTE: You may be able to switch this to vmware here as there is a vmware box as well, but i have not tested this.
• win2k8 -- this is the name of the vulnerable box. There's also a ub1404 ubuntu box on this Vagrantfile, which shows you how old this is. I wouldn't recommend using that. Instead, probably use Kali or Parrot.

Step 7 -- Find IP

Once your box is running, grab the IP. There's likely a better way to do this, but I just ask the box for it's IP directly:

OPENSSL_CONF=$PWD/openssl.cnf MS3_DIFFICULTY=easy vagrant winrm win2k8 -c ipconfig

Your routing might be different. In my testing, the routed IP is 192.168.56.x, which is a default VirtualBox internal address space. If you change your adapter or using vmware, this might be different.

Step 8 -- Snapshot and shutdown

It may be helpful to create a snapshot initially so if you break anything you can revert:

# Halt the box
OPENSSL_CONF=$PWD/openssl.cnf MS3_DIFFICULTY=easy vagrant halt win2k8
# Create snapshot
OPENSSL_CONF=$PWD/openssl.cnf MS3_DIFFICULTY=easy vagrant snapshot save win2k8 base
# Later restore with
OPENSSL_CONF=$PWD/openssl.cnf MS3_DIFFICULTY=easy vagrant snapshot restore win2k8 base

Check out the vulnerabilities: https://github.com/rapid7/metasploitable3/wiki/Vulnerabilities

Happy learning!

openssl.cnf

#
# OpenSSL example configuration file.
# See doc/man5/config.pod for more info.
#
# This is mostly being used for generation of certificate requests,
# but may be used for auto loading of providers

# Note that you can include other files from the main configuration
# file using the .include directive.
#.include filename

# This definition stops the following lines choking if HOME isn't
# defined.
HOME			= .

 # Use this in order to automatically load providers.
openssl_conf = openssl_init

# Comment out the next line to ignore configuration errors
config_diagnostics = 1

# Extra OBJECT IDENTIFIER info:
# oid_file       = $ENV::HOME/.oid
oid_section = new_oids

# To use this configuration file with the "-extfile" option of the
# "openssl x509" utility, name here the section containing the
# X.509v3 extensions to use:
# extensions		=
# (Alternatively, use a configuration file that has only
# X.509v3 extensions in its main [= default] section.)

[ new_oids ]
# We can add new OIDs in here for use by 'ca', 'req' and 'ts'.
# Add a simple OID like this:
# testoid1=1.2.3.4
# Or use config file substitution like this:
# testoid2=${testoid1}.5.6

# Policies used by the TSA examples.
tsa_policy1 = 1.2.3.4.1
tsa_policy2 = 1.2.3.4.5.6
tsa_policy3 = 1.2.3.4.5.7

# For FIPS
# Optionally include a file that is generated by the OpenSSL fipsinstall
# application. This file contains configuration data required by the OpenSSL
# fips provider. It contains a named section e.g. [fips_sect] which is
# referenced from the [provider_sect] below.
# Refer to the OpenSSL security policy for more information.
# .include fipsmodule.cnf

[openssl_init]
providers = provider_sect
ssl_conf = ssl_sect

# List of providers to load
[provider_sect]
default = default_sect
legacy = legacy_sect

# The fips section name should match the section name inside the
# included fipsmodule.cnf.
# fips = fips_sect

# If no providers are activated explicitly, the default one is activated implicitly.
# See man 7 OSSL_PROVIDER-default for more details.
#
# If you add a section explicitly activating any other provider(s), you most
# probably need to explicitly activate the default provider, otherwise it
# becomes unavailable in openssl.  As a consequence applications depending on
# OpenSSL may not work correctly which could lead to significant system
# problems including inability to remotely access the system.
[default_sect]
activate = 1

[legacy_sect]
activate = 1

####################################################################
[ ca ]
default_ca	= CA_default		# The default ca section

####################################################################
[ CA_default ]

dir		= ./demoCA		# Where everything is kept
certs		= $dir/certs		# Where the issued certs are kept
crl_dir		= $dir/crl		# Where the issued crl are kept
database	= $dir/index.txt	# database index file.
#unique_subject	= no			# Set to 'no' to allow creation of
					# several certs with same subject.
new_certs_dir	= $dir/newcerts		# default place for new certs.

certificate	= $dir/cacert.pem 	# The CA certificate
serial		= $dir/serial 		# The current serial number
crlnumber	= $dir/crlnumber	# the current crl number
					# must be commented out to leave a V1 CRL
crl		= $dir/crl.pem 		# The current CRL
private_key	= $dir/private/cakey.pem# The private key

x509_extensions	= usr_cert		# The extensions to add to the cert

# Comment out the following two lines for the "traditional"
# (and highly broken) format.
name_opt 	= ca_default		# Subject Name options
cert_opt 	= ca_default		# Certificate field options

# Extension copying option: use with caution.
# copy_extensions = copy

# Extensions to add to a CRL. Note: Netscape communicator chokes on V2 CRLs
# so this is commented out by default to leave a V1 CRL.
# crlnumber must also be commented out to leave a V1 CRL.
# crl_extensions	= crl_ext

default_days	= 365			# how long to certify for
default_crl_days= 30			# how long before next CRL
default_md	= default		# use public key default MD
preserve	= no			# keep passed DN ordering

# A few difference way of specifying how similar the request should look
# For type CA, the listed attributes must be the same, and the optional
# and supplied fields are just that :-)
policy		= policy_match

# For the CA policy
[ policy_match ]
countryName		= match
stateOrProvinceName	= match
organizationName	= match
organizationalUnitName	= optional
commonName		= supplied
emailAddress		= optional

# For the 'anything' policy
# At this point in time, you must list all acceptable 'object'
# types.
[ policy_anything ]
countryName		= optional
stateOrProvinceName	= optional
localityName		= optional
organizationName	= optional
organizationalUnitName	= optional
commonName		= supplied
emailAddress		= optional

####################################################################
[ req ]
default_bits		= 2048
default_keyfile 	= privkey.pem
distinguished_name	= req_distinguished_name
attributes		= req_attributes
x509_extensions	= v3_ca	# The extensions to add to the self signed cert

# Passwords for private keys if not present they will be prompted for
# input_password = secret
# output_password = secret

# This sets a mask for permitted string types. There are several options.
# default: PrintableString, T61String, BMPString.
# pkix	 : PrintableString, BMPString (PKIX recommendation before 2004)
# utf8only: only UTF8Strings (PKIX recommendation after 2004).
# nombstr : PrintableString, T61String (no BMPStrings or UTF8Strings).
# MASK:XXXX a literal mask value.
# WARNING: ancient versions of Netscape crash on BMPStrings or UTF8Strings.
string_mask = utf8only

# req_extensions = v3_req # The extensions to add to a certificate request

[ req_distinguished_name ]
countryName			= Country Name (2 letter code)
countryName_default		= AU
countryName_min			= 2
countryName_max			= 2

stateOrProvinceName		= State or Province Name (full name)
stateOrProvinceName_default	= Some-State

localityName			= Locality Name (eg, city)

0.organizationName		= Organization Name (eg, company)
0.organizationName_default	= Internet Widgits Pty Ltd

# we can do this but it is not needed normally :-)
#1.organizationName		= Second Organization Name (eg, company)
#1.organizationName_default	= World Wide Web Pty Ltd

organizationalUnitName		= Organizational Unit Name (eg, section)
#organizationalUnitName_default	=

commonName			= Common Name (e.g. server FQDN or YOUR name)
commonName_max			= 64

emailAddress			= Email Address
emailAddress_max		= 64

# SET-ex3			= SET extension number 3

[ req_attributes ]
challengePassword		= A challenge password
challengePassword_min		= 4
challengePassword_max		= 20

unstructuredName		= An optional company name

[ usr_cert ]

# These extensions are added when 'ca' signs a request.

# This goes against PKIX guidelines but some CAs do it and some software
# requires this to avoid interpreting an end user certificate as a CA.

basicConstraints=CA:FALSE

# This is typical in keyUsage for a client certificate.
# keyUsage = nonRepudiation, digitalSignature, keyEncipherment

# PKIX recommendations harmless if included in all certificates.
subjectKeyIdentifier=hash
authorityKeyIdentifier=keyid,issuer

# This stuff is for subjectAltName and issuerAltname.
# Import the email address.
# subjectAltName=email:copy
# An alternative to produce certificates that aren't
# deprecated according to PKIX.
# subjectAltName=email:move

# Copy subject details
# issuerAltName=issuer:copy

# This is required for TSA certificates.
# extendedKeyUsage = critical,timeStamping

[ v3_req ]

# Extensions to add to a certificate request

basicConstraints = CA:FALSE
keyUsage = nonRepudiation, digitalSignature, keyEncipherment

[ v3_ca ]


# Extensions for a typical CA


# PKIX recommendation.

subjectKeyIdentifier=hash

authorityKeyIdentifier=keyid:always,issuer

basicConstraints = critical,CA:true

# Key usage: this is typical for a CA certificate. However since it will
# prevent it being used as an test self-signed certificate it is best
# left out by default.
# keyUsage = cRLSign, keyCertSign

# Include email address in subject alt name: another PKIX recommendation
# subjectAltName=email:copy
# Copy issuer details
# issuerAltName=issuer:copy

# DER hex encoding of an extension: beware experts only!
# obj=DER:02:03
# Where 'obj' is a standard or added object
# You can even override a supported extension:
# basicConstraints= critical, DER:30:03:01:01:FF

[ crl_ext ]

# CRL extensions.
# Only issuerAltName and authorityKeyIdentifier make any sense in a CRL.

# issuerAltName=issuer:copy
authorityKeyIdentifier=keyid:always

[ proxy_cert_ext ]
# These extensions should be added when creating a proxy certificate

# This goes against PKIX guidelines but some CAs do it and some software
# requires this to avoid interpreting an end user certificate as a CA.

basicConstraints=CA:FALSE

# This is typical in keyUsage for a client certificate.
# keyUsage = nonRepudiation, digitalSignature, keyEncipherment

# PKIX recommendations harmless if included in all certificates.
subjectKeyIdentifier=hash
authorityKeyIdentifier=keyid,issuer

# This stuff is for subjectAltName and issuerAltname.
# Import the email address.
# subjectAltName=email:copy
# An alternative to produce certificates that aren't
# deprecated according to PKIX.
# subjectAltName=email:move

# Copy subject details
# issuerAltName=issuer:copy

# This really needs to be in place for it to be a proxy certificate.
proxyCertInfo=critical,language:id-ppl-anyLanguage,pathlen:3,policy:foo

####################################################################
[ tsa ]

default_tsa = tsa_config1	# the default TSA section

[ tsa_config1 ]

# These are used by the TSA reply generation only.
dir		= ./demoCA		# TSA root directory
serial		= $dir/tsaserial	# The current serial number (mandatory)
crypto_device	= builtin		# OpenSSL engine to use for signing
signer_cert	= $dir/tsacert.pem 	# The TSA signing certificate
					# (optional)
certs		= $dir/cacert.pem	# Certificate chain to include in reply
					# (optional)
signer_key	= $dir/private/tsakey.pem # The TSA private key (optional)
signer_digest  = sha256			# Signing digest to use. (Optional)
default_policy	= tsa_policy1		# Policy if request did not specify it
					# (optional)
other_policies	= tsa_policy2, tsa_policy3	# acceptable policies (optional)
digests     = sha1, sha256, sha384, sha512  # Acceptable message digests (mandatory)
accuracy	= secs:1, millisecs:500, microsecs:100	# (optional)
clock_precision_digits  = 0	# number of digits after dot. (optional)
ordering		= yes	# Is ordering defined for timestamps?
				# (optional, default: no)
tsa_name		= yes	# Must the TSA name be included in the reply?
				# (optional, default: no)
ess_cert_id_chain	= no	# Must the ESS cert id chain be included?
				# (optional, default: no)
ess_cert_id_alg		= sha1	# algorithm to compute certificate
				# identifier (optional, default: sha1)

[insta] # CMP using Insta Demo CA
# Message transfer
server = pki.certificate.fi:8700
# proxy = # set this as far as needed, e.g., http://192.168.1.1:8080
# tls_use = 0
path = pkix/

# Server authentication
recipient = "/C=FI/O=Insta Demo/CN=Insta Demo CA" # or set srvcert or issuer
ignore_keyusage = 1 # potentially needed quirk
unprotected_errors = 1 # potentially needed quirk
extracertsout = insta.extracerts.pem

# Client authentication
ref = 3078 # user identification
secret = pass:insta # can be used for both client and server side

# Generic message options
cmd = ir # default operation, can be overridden on cmd line with, e.g., kur

# Certificate enrollment
subject = "/CN=openssl-cmp-test"
newkey = insta.priv.pem
out_trusted = insta.ca.crt
certout = insta.cert.pem

[pbm] # Password-based protection for Insta CA
# Server and client authentication
ref = $insta::ref # 3078
secret = $insta::secret # pass:insta

[signature] # Signature-based protection for Insta CA
# Server authentication
trusted = insta.ca.crt # does not include keyUsage digitalSignature

# Client authentication
secret = # disable PBM
key = $insta::newkey # insta.priv.pem
cert = $insta::certout # insta.cert.pem

[ir]
cmd = ir

[cr]
cmd = cr

[kur]
# Certificate update
cmd = kur
oldcert = $insta::certout # insta.cert.pem

[rr]
# Certificate revocation
cmd = rr
oldcert = $insta::certout # insta.cert.pem

[ssl_sect]
system_default = system_default_sect

[system_default_sect]
CipherString = DEFAULT:@SECLEVEL=2