o365spray

For educational, authorized and/or research purposes only.

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.

If any bugs/errors are encountered, please open an Issue with the details (or a Pull Request with the proposed fix). See the section below for more information about using previous versions.

Usage

Validate a domain is using O365:
o365spray --validate --domain test.com

Perform username enumeration against a given domain:
o365spray --enum -U usernames.txt --domain test.com

Perform password spraying against a given domain:
o365spray --spray -U usernames.txt -P passwords.txt --count 2 --lockout 5 --domain test.com

usage: o365spray [-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] [--rate RATE] [--safe SAFE]
                 [--timeout TIMEOUT] [--proxy PROXY] [--output OUTPUT]
                 [-v] [--debug]

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.

Modules

o365spray has been packaged to allow for use within automation scenarios. If domain validation, user enumeration, or password spraying is a part of your proposed attack/recon automation, see the below modules and import usage exmaples.

Validation

getuserrealm
openid-config -- Currently Disabled

The validator can be imported and used via:

from o365spray.core import Validator
v = Validator()
valid, adfs_url = v.validate('domain.com')

Enumeration

office
oauth2
onedrive
activesync -- Currently Disabled
autodiscover -- Currently Disabled

The onedrive module relies on the target user(s) having previously logged into OneDrive. If a valid user has not yet used OneDrive, their account will show as 'invalid'.

The enumerator can be imported and used via:

from o365spray.core import Enumerator
loop = asyncio.get_event_loop()
e = Enumerator(loop, writer=False)
loop.run_until_complete(
    e.run(
        userlist,
        password,
        domain,
        module,
    )
)
loop.run_until_complete()
loop.close()
list_of_valid_users = e.VALID_ACCOUNTS

Spraying

oauth2
activesync
autodiscover
reporting
adfs

The oAuth2 module can be used for federated spraying, but it should be noted that this will work ONLY when the target has enabled password synchronization - otherwise authentication will always fail. The default mechanic is to default to the 'adfs' module when federation is identified.

The sprayer can be imported and used via:

from o365spray.core import Sprayer
loop = asyncio.get_event_loop()
s = Sprayer(loop, writer=False)
loop.run_until_complete(
    s.run(
        password,
        domain,
        module,
        userlist,
    )
)
loop.run_until_complete()
loop.close()
list_of_valid_creds = s.VALID_CREDENTIALS

Omnispray

The o365spray framework has been ported to a new tool: Omnispray. This tool is meant to modularize the original enumeration and spraying framework to allow for generic targeting, not just O365. Omnispray includes template modules for enumeration and spraying that can be modified and leveraged for any target.

Acknowledgments

Author	Tool/Research	Link
gremwell	o365enum: User enumeration via office.com without authentication	o365enum
grimhacker	office365userenum: ActiveSync user enumeration research and discovery.	office365userenum / blog post
Raikia	UhOh365: User enumeration via Autodiscover without authentication.	UhOh365
dafthack	MSOLSpray: Password spraying via MSOL	MSOLSpray
byt3bl33d3r	MSOLSpray: Python reimplementation	Gist
nyxgeek	onedrive_user_enum: OneDrive user enumeration	onedrive_user_enum / blog post
Mr-Un1k0d3r	adfs-spray: ADFS password spraying	adfs-spray
Nestori Syynimaa	AADInternals: oAuth2 user enumeration	AADInternals
Daniel Chronlund / xFreed0m	Invoke-AzureAdPasswordSprayAttack / ADFSpray: Office 365 reporting API password spraying	Invoke-AzureAdPasswordSprayAttack / ADFSpray
byt3bl33d3r	SprayingToolkit: Code references	SprayingToolkit
sensepost	ruler: Code references	Ruler

Using Previous Versions

o365spray was recently rewritten (v2) and could have some hidden bugs remaining. If issues are encountered, try checking out the commit prior to the code rewrite (v1.3.7):

git checkout e235abdcebad61dbd2cde80974aca21ddb188704

MathzRocha/o365spray