The Metasploit Framework (MSF)
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⚡ Prerequisites
Basic familiarity with Linux & Windows
Basic familiarity with TCP & UDP protocols
📕 Learning Objectives
Understand, install, configure and use Metasploit Framework
Perform info-gathering, enumeration, exploitation, post exploitation with Metasploit
🔬 Training list - PentesterAcademy/INE Labs
subscription required
Provides automation of the penetration testing life cycle (specially exploitation and post-exploitation)
Used to develop and test exploits
Has a world database and public tested exploits
It is modular, new modules can be added and integrated
Metasploit Framework is the Community Edition
Metasploit Pro & Express are Commercial versions
Interface
Methods of interacting with the Metasploit Framework (msfconsole, Metasploit cmd)
Module
Pieces of code that perform a particular task (an exploit)
Vulnerability
Exploitable flaw or weakness in a computer system or network
Exploit
Code/Module used to take advantage of a vulnerability
Payload
Piece of code delivered to the target by an exploit (execute arbitrary commands or provide remote access)
Listener
Utility that listens for an incoming connection from a target
📌 Exploit is launched (takes advantage of the vulnerability) ➡️ Payload dropped (executes a reverse shell command) ➡️ Connects back to the Listener
Discontinued in 2015, MSFconsole can be used with the same functionality of redirecting output from other tools into msfcli and vice versa.
🗒️ Metasploit Community Edition GUI - a web based GUI front-end of the MSF.
Visualizes targets and simplifies network discovery
Recommends exploits
Exposes the advanced capabilities of the MSF
🗒️ A module is the piece of code that can be utilized and executed by the MSF.
The MSF libraries (Rex, Core, Base) allow to extend and initiate functionality, facilitating the execution of modules without having to write additional code.
Exploit
Used to take advantage of a vulnerability, usually paired with a payload
Payload
Code delivered and remotely executed on the target after successful exploitation - e.g. a reverse shell that initiates a connection
Encoder
NOPS
Keep the payload sizes consistent across exploit attempts and ensure the stability of a payload on the target system
Auxiliary
Is not paired with a payload, used to perform additional functionality - e.g. port scanners, fuzzers, sniffers, etc
Payloads are created at runtime from various components. Depending on the target system and infrastructure, there are two types of payloads that can be used:
Non-Staged Payload - sent to the target system as is, along with the exploit
Staged Payload - sent to the target in two parts:
the stager (first part) establish a stable communication channel between the attacker and target. It contains a payload, the stage, that initiates a reverse connection back to the attacker
the stage (second part) is downloaded by the stager and executed
executes arbitrary commands on the target
provides a reverse shell or Meterpreter session
Communicates over the stager socket
Provides an interactive command interpreter on the target system
MSF filesystem is intuitive and organized by directories.
Modules are stored under:
/usr/share/metasploit-framework/modules/
~/.msf4/modules - user specified modules
can be adopted as a roadmap for Metasploit integration and understanding of the phases of a penetration test.
The various phases involved in a typical pentest should be:
📌 Pre-Engagement Interactions
⬇️
📌 Information Gathering
⬇️
📌 Enumeration
Threat Modeling
Vulnerability Analysis
⬇️
📌 Exploitation
Identify Vulnerable Services
Prepare Exploit Code
Gaining Access
Bypass AV detection
Pivoting
⬇️
📌 Post Exploitation
Privilege Escalation
Maintaining Persistent Access
Clearing Tracks
⬇️
📌 Reporting
Information Gathering & Enumeration
Auxiliary Modules, nmap reports
Vulnerability Scanning
Auxiliary Modules, nessus reports
Exploitation
Exploit Modules & Payloads
Post Exploitation
Meterpreter
Privilege Escalation
Post Exploitation Modules, Meterpreter
Maintaining Persistent Access
Post Exploitation Modules, Persistence
🗒️ The Metasploit Framework Database (msfdb) contains all the data used with MSF like assessments and scans data, etc.
Uses PostgreSQL as the primary database - postgresql service must be running
Facilitates the import and storage of scan results (from Nmap, Nessus, other tools)
Use APT package manager on Kali Linux (or on Debian-based distros)
Enable postgresql at boot, start the service and initialize MSF database
Run msfconsole to start the Metasploit Framework Console
Check the db connection is on in the msfconsole
Deploying a Kali Linux virtual machine with Metasploit pre-installed
Setting up a target in a virtual lab, Metasploitable3, with Vagrant
A sample walkthrough against a vulnerable MySQL Server
Frequently Asked Questions (FAQ)
🗒️ The Metasploit Framework Console (msfconsole) is an all-in-one interface and centralized console that allows access to all of the MSF options and features.
It is launched by running the msfconsole command
Run it in quiet mode without the banner with
An MSF module requires additional information that can be configured through the use of MSF variables, both local or global variables, called options inside the msfconsole.
Variables e.g. (they are based on the selected module):
LHOST - attacker's IP address
LPORT - attacker's port number (receive reverse connection)
RHOST - target's IP address
RHOSTS - multiple targets/networks IP addresses
RPORT - target port number
Run msfconsole and check these useful commands:
🗒️ Metasploit Workspaces allows to manage and organize the hosts, data, scans and activities stored in the msfdb.
Import, manipulate, export data
Create, manage, switch between workspaces
Sort and organize the assessments of the penetration test
📌 It's recommended to create a new workspace for each engagement.
Create a new workspace
Change workspace
Delete a workspace
The Metasploit Framework allows to import nmap results.
nmap enumeration results (service versions, operating systems, etc) can be exported into a file that can be imported into MSF and used for further detection and exploitation.
Some commands:
Output the nmap scan results into an .XML format file that can be imported into MSF
In the same lab environment from above, use msfconsole to import the results into MSF with the db_import command
Inside msfconsole
Perform an nmap scan within the MSF Console and import the results in a dedicated workspace
MSF Auxiliary modules are used during the information gathering (similar to nmap) and the post exploitation phases of the pentest.
perform TCP/UDP port scanning
enumerate services
discover hosts on different network subnets (post-exploitation phase)
Exploitation
Perform a network scan on the second target
Add the route within meterpreter and background the meterpreter session
Upload and run nmap against the second target, from the first target machine
📌 There are
3running services on the second target machine.
Into msfconsole
Next, there are some MSF commands and modules for service enumeration on the same labs from the Enumeration Section.
Auxiliary modules can be used for enumeration, brute-force attacks, etc
❗📝 On every attacker machine, run this command to start msfconsole:
Setup a global variable. This will set the RHOSTS option for all the modules utilized:
auxiliary/scanner/ftp/ftp_version
auxiliary/scanner/ftp/ftp_login
auxiliary/scanner/ftp/anonymous
auxiliary/scanner/smb/smb_version
auxiliary/scanner/smb/smb_enumusers
auxiliary/scanner/smb/smb_enumshares
Remember to specify the correct port and if targeting a web server with SSL enabled, in the options.
auxiliary/scanner/http/apache_userdir_enum
auxiliary/scanner/http/brute_dirs
auxiliary/scanner/http/dir_scanner
auxiliary/scanner/http/dir_listing
auxiliary/scanner/http/http_put
auxiliary/scanner/http/files_dir
auxiliary/scanner/http/http_login
auxiliary/scanner/http/http_header
auxiliary/scanner/http/http_version
auxiliary/scanner/http/robots_txt
auxiliary/admin/mysql/mysql_enum
auxiliary/admin/mysql/mysql_sql
auxiliary/scanner/mysql/mysql_file_enum
auxiliary/scanner/mysql/mysql_hashdump
auxiliary/scanner/mysql/mysql_login
auxiliary/scanner/mysql/mysql_schemadump
auxiliary/scanner/mysql/mysql_version
auxiliary/scanner/mysql/mysql_writable_dirs
Check the MySQL Enumerated data within MSF:
auxiliary/scanner/ssh/ssh_version
auxiliary/scanner/ssh/ssh_login
This module sets up SSH sessions
auxiliary/scanner/ssh/ssh_enumusers
auxiliary/scanner/smtp/smtp_enum
auxiliary/scanner/smtp/smtp_version
MSF Auxiliary and exploit modules can be utilized to identify inherent vulnerabilities in services, O.S. and web apps.
Useful in the Exploitation phase of the pentest
Metasploitable3 is a vulnerable virtual machine developed by Rapid7, intended to be used as a vulnerable target for testing exploits with Metasploit.
Kali Linux attacker machine must be configured with the same local network of the Metasploitable3 VMs.
Detect active hosts on the local network, from the Kali VM:
Run Metasploit:
Service version is a key piece of information for the vulnerabilities scanning. Use the db_nmap command inside the MSF
Manually search for a specific exploit
Check if there are any exploits for a particular version of a service
Check if a module will work on the specific version of the service
Back in msfconsole, check if the server is vulnerable to MS17-010
takes a look at the Metasploit database and provides a list of exploit modules to use for the already enumerated services
On a Kali terminal
On msfconsole
On msfconsole use the analyze command to auto analyze the contents of the MSFdb (hosts & services)
A vulnerability scan with Nessus result can be imported into the MSF for analysis and exploitation.
Nessus Essentials free version allows to scan up to 16 IPs.
Start Nessus Essentials on the Kali VM, login and create a New Basic Network Scan and run it.
Wait for the scan conclusion and export the results with the Export/Nessus button.
Open the msfconsole terminal and import the Nessus results
Check the information from the scan results with the hosts, services, vulns commands
🗒️ WMAP is a web application vulnerability scanner that allows to conduct and automate web server enumeration and scanning from within the Metasploit Framework.
Available as a fully integrated MSF plugin
Utilizes the in-built MSF auxiliary modules
Load WMAP extension within msfconsole
Add WMAP site
Specify the target URL
Show only the MSF modules that will be able to be run against target
Run the web app vulnerability scan
this will run all enabled modules against the target web server
Analyze the results produced by WMAP.
List WMAP found vulnerabilities
Since the allowed methods are POST, OPTIONS, GET, HEAD, exploit the vulnerability with the use of auxiliary/scanner/http/http_put module to upload a file into the /data directory
📌 A reverse shell payload can be uploaded and run on the target.
Test if the file has been uploaded correctly
A client-side attack is a security breach that happens on the client side.
Social engineering techniques take advantage of human vulnerabilities
Require user-interaction to open malicious documents or portable executables (PEs)
The payload is stored on the client's system
Attackers have to pay attention to Anti Virus detection
❗ Advanced modern antivirus solutions detects and blocks this type of payloads very easily.
e.g.- generate a malicious meterpreter payload, transfer it to a client target; once executed it will connect back to the payload handler and provides with remote access
List available payloads
When generating a payload the exact name of the payload must be specified
target operating system
target O.S. architecture (x64, x86 ...)
payload type
protocol used to connect back (depends on requirements)
e.g. of Staged payload
windows/x64/meterpreter/reverse_tcp
e.g. of Non-Staged payload
windows/x64/meterpreter_reverse_https
Generate a Windows payload with msfvenom
32bit payload:
64bit payload:
List the output formats available
Generate a Linux payload with msfvenom
32bit payload:
64bit payload:
📌 Platform and architecture are auto selected if not specified, based on the selected payload
The transferring method onto the target system depends on the type of the social engineering technique.
e.g. A simple web server can be set up on the attacker system to serve the payload files and a handler to receive the connection back from the target system
To deal with a meterpreter payload, an appropriate listener is necessary to handle the reverse connection, the multi/handler Metasploit module in this case
Download the payload on the Windows 2008 system (in this case my home lab VM) from this link
http://192.168.31.128:8080
Run the payloadx86.exe payload on the target
The meterpreter session on the attacker machine should be opened
Same example with the linux/x86/meterpreter/reverse_tcp Linux payload executed on the Kali VM.
Signature based Antivirus solutions can detect malicious files or executables. Older AV solutions can be evaded by encoding the payloads.
❗ This kind of attack vector is outdated and hardly used today.
May work on legacy old O.S. like Windows 7 or older.
🗒️ Payload Encoding involves changing the payload shellcode with the aim of changing the payload signature.
🗒️ Shellcode is the code typically used as a payload for exploitation, that provides with a remote command shell on the target system.
Excellent encoders are cmd/powershell_base64 and x86/shikata_ga_nai
Generate a Win x86 payload and encode it with shikata_ga_nai:
The payload can be encoded as often as desired by increasing the number of iterations.
The more iterations, the better chances to bypass an Antivirus. Use -i option.
Test each of the above generated payloads, like before
📌 Modern antivirus detects and blocks the encoded payload as soon as the download is started:
Payloads can be injected into PEs with msfvenom with the -x and -k options
Transfer and run the winrar.exe file to the target O.S.
File description is kept, but not its functionality.
Proceed with the Post Exploitation module to migrate the process into another one, in the meterpreter session
Repetitive tasks and commands can be automated using MSF resource scripts (same as batch scripts).
Almost every MSF command can be automated.
e.g. 1
Automate the process of setting up a handler for the generated payloads, by creating a new handler.rc file
Load and run the recourse script in msfconsole
e.g. 2
e.g. 3
📌 Load up a resource script from within the msfconsole with the resource command
Typed in commands in a new msfconsole session, can be exported in a new resource script
A HFS (HTTP File Server) is a file and documents sharing web server.
Rejetto HFS - free open source HTTP file server
EternalBlue takes advantage of a Windows SMBv1 protocol vulnerability
Patch was released in March 2017
Some MSF useful commands from my Home Lab (Kali VM + Win 2008_R2 Server)
Identify WinRM users with MSF and exploit WinRM by obtaining access credentials.
Default WinRM HTTP port is 5985 and HTTPS 5986
Tomcat default TCP port is 8080
Apache web server host HTML/PHP web apps, instead
Apache Tomcat < v.8.5.23 is vulnerable to a JSP Upload Bypass / RCE
vsftpd v.2.3.4 is vulnerable to a command execution vulnerability
Samba is the Linux implementation of SMB.
Samaba v.3.5.0 is vulnerable to a RCE vulnerability
libssh is a C library that implements the SSHv2 protocol
SSH default TCP port is 22
libssh v.0.6.0 - 0.8.0 is vulnerable to an authentication bypass vulnerability
SMTP default TCP port is 25
other TCP ports are 465 and 587
Haraka prior to v.2.8.9 is vulnerable to command injection
🗒️ Post Exploitation is the process of gaining further information or access to the target's internal network, after the initial exploitation phase, using various techniques like:
local enumeration
maintaining persistent access
dumping hashes
covering tracks
There are many post exploitation modules provided by the MSF.
🗒️ Persistence consists of techniques used by adversaries to maintain access to systems across restarts, changed credentials, or other interruptions.
🗒️ Pivoting is a post exploitation technique of using a compromised host, a foothold / plant, to attack other systems on its private internal network.
Facilitates the execution of system commands, file system navigation, keylogging
Load custom scripts and plugins dynamically
📌 MSF has various types of Meterpreter payloads based on the target environment
Windows post exploitation MSF modules can be used to:
Enumerate user privileges, logged-on users, installed programs, antiviruses, computers connected to a domain, installed patches and shares
VM check
🗒️ Windows Event Logs, accessed via the Event Viewer on Windows, are categorized into:
Application logs - apps startups, crashes, etc
System logs - system startups, reboots, etc
Security logs - password changes, authentication failures/success, etc
Clearing event logs is an important part of the system assessment.
Linux post exploitation MSF modules can be used to:
Enumerate system configuration, environment variables, network configuration, user's history
VM check
🗒️ Armitage is a Java-based GUI front-end for the MSF.
Automate port scanning, exploitation, post exploitation
Visualize targets
Requires MSFdb and services to be running
Pre-packed with Kali Linux
🔬 Port Scanning & Enumeration With Armitage - lab by INE
Victim Machine 1:
10.2.21.86Victim Machine 2:
10.2.25.150
Hosts - Add Hosts
Add victim 1 IP
Set the lab as Victim 1
Right-click the target and Scan it
Check Services
Perform an Nmap Scan from the Hosts menu
Check Services
Search for rejetto and launch the exploit module
Try Dump Hashes via the registry method
Saved hashes can be found under the View - Loot menu
Browse Files
Show Processes
Setup Pivoting
Add, Enumerate and Exploit Victim 2
Port forward the port 80 and use nmap
Remove the created localhost 127.0.0.1
Search for BadBlue and use the badblue_passthru exploit on Victim 2
Migrate to an x64 from the Processes tab
Dump hashes with the lsass method
🗒️ The (MSF) is an open-source pentesting and exploit development platform, used to write, test and execute exploit code.
It is
Founded by H.D. Moore in 2003 (developed in Perl), Written in Ruby in 2007, acquired by in 2009, released as Metasploit v6.0 in 2020
📌 Check the
🗒️ Metasploit Framework Console () - an all in one interface that provides with access to all the functionality of the MSF.
🗒️ Metasploit Framework Command Line Interface () - a command line utility used to facilitate the creation of automation scripts that utilize Metasploit modules.
🗒️ - a free Java based GUI front-end cyber attack management tool for the MSF.
Used to encode payloads in order to avoid Anti Virus detection - e.g. encoding scheme
🗒️ The is an advanced multi-functional payload executed by in memory DLL injection stagers on the target system.
🗒️ (Penetration Testing Execution Standard) is a methodology that contains 7 main sections, defined by the standard as a comprehensive basis for penetration testing execution.
📌 Check this article by StationX ➡️ which will cover:
🔬 Check the full nmap information gathering lab in (at the end of the page).
🔬 Lab
📌🔬 Check the for basic nmap enumeration.
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🔬 lab environment will be used for the vulnerability scanning demonstration.
🔬 You can find my lab installation & configuration with Vagrant at , set up for educational purposes.
Use tool from the Kali terminal, instead of search MSF command, by displaying only the Metasploit exploit modules
- a Metasploit plugin for easy exploit & vulnerability attack.
🔬 You can find my .
🔬 The lab is the same one from the HTTP Metasploit Enumeration section above -
- a Metasploit standalone payload generator and encoder
🗒️ (PE) is a file format for executables, object code, DLLs and others, used in 32-bit and 64-bit Windows O.S.
Download a portable executable, e.g.
🔬
🔬 Check the
🔬
is a free open source Java servlet web server, build to host dynamic websites and web apps developed in Java.
🔬
is an Unix FTP server.
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is an open source high performance SMTP server developed in Node.js
🔬
🗒️ is the action of (secretly) recording/capturing the keystrokes entered on a target system.
🔬 Check the for various Meterpreter commands and techniques examples and how to upgrade shells to Meterpreter sessions.
🔬 Check out the with post-exploitation techniques for various Windows services.
🔬 Check out the with post-exploitation techniques for various Unix services.
