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https://github.com/gremwell/o365enum

Enumerate valid usernames from Office 365 using ActiveSync, Autodiscover v1, or office.com login page.
https://github.com/gremwell/o365enum

office365 security user-enumeration

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Enumerate valid usernames from Office 365 using ActiveSync, Autodiscover v1, or office.com login page.

Host: GitHub
URL: https://github.com/gremwell/o365enum
Owner: gremwell
Created: 2020-02-18T12:22:50.000Z (almost 5 years ago)
Default Branch: master
Last Pushed: 2024-05-02T07:45:31.000Z (7 months ago)
Last Synced: 2024-08-03T21:01:45.569Z (4 months ago)
Topics: office365, security, user-enumeration
Language: Python
Homepage: https://www.gremwell.com/blog/office365-user-enumeration
Size: 33.2 KB
Stars: 230
Watchers: 8
Forks: 38
Open Issues: 2
Metadata Files:
- Readme: README.md

Awesome Lists containing this project

Awesome-Azure-Pentest - Office 365 User Enumeration - Enumerate valid usernames from Office 365 using ActiveSync, Autodiscover v1 or office.com login page (Tools / Enumeration)

README

# Office 365 User Enumeration

Enumerate valid usernames from Office 365 using ActiveSync, Autodiscover, or office.com login page.

## Usage

o365enum will read usernames from the file provided as first parameter. The file should have one username per line. The output is CSV-based for easier parsing. Valid status can be 0 (invalid user), 1 (valid user), 2 (valid user and valid password).

```
python3.6 o365enum.py -h
usage: o365enum.py [-h] -u USERLIST [-p PASSWORD] [-n NUM] [-v]
[-m {activesync,autodiscover,office.com}]

Office365 User Enumeration Script

optional arguments:
-h, --help show this help message and exit
-u USERLIST, --userlist USERLIST
username list one per line (default: None)
-p PASSWORD, --password PASSWORD
password to try (default: Password1)
-n NUM, --num NUM # of reattempts to remove false negatives (default: 3)
-v, --verbose Enable verbose output at urllib level (default: False)
-m {activesync,autodiscover,office.com}, --method {activesync,autodiscover,office.com}
method to use (default: activesync)
```

Example run:

```
./o365enum.py -u users.txt -p Password2 -n 1 -m activesync
username,valid
[email protected],0
[email protected],1
```

## Enumeration Methods

### ActiveSync Enumeration

This method is based on grimhacker's [method](https://grimhacker.com/2017/07/24/office365-activesync-username-enumeration/) that sends Basic HTTP authentication requests to ActiveSync endpoint. However, **checking the status code no longer works given that Office365 returns a 401 whether the user exists or not**.

Instead, we send the same request but check for a custom HTTP response header (`X-MailboxGuid`) presence to identify whether a username is valid or not.

#### Existing Account

The request below contains the following Base64 encoded credentials in the Authorization header: [email protected]:Password1

```
OPTIONS /Microsoft-Server-ActiveSync HTTP/1.1
Host: outlook.office365.com
Connection: close
MS-ASProtocolVersion: 14.0
Content-Length: 0
Authorization: Basic dmFsaWRfdXNlckBjb250b3NvLmNvbTpQYXNzd29yZDE=
```

This elicits the following response ("401 Unauthorized") with the `X-MailboxGuid` header set, indicating that the username is valid but the password is not:

```
Date: Fri, 31 Jan 2020 13:02:46 GMT
Connection: close
HTTP/1.1 401 Unauthorized
Content-Length: 1293
Content-Type: text/html
Server: Microsoft-IIS/10.0
request-id: d494a4bc-3867-436a-93ef-737f9e0522eb
X-CalculatedBETarget: AM0PR09MB2882.eurprd09.prod.outlook.com
X-BackEndHttpStatus: 401
X-RUM-Validated: 1
X-MailboxGuid: aadaf467-cd08-4a23-909b-9702eca5b845 <--- This header leaks the account status (existing)
X-DiagInfo: AM0PR09MB2882
X-BEServer: AM0PR09MB2882
X-Proxy-RoutingCorrectness: 1
X-Proxy-BackendServerStatus: 401
X-Powered-By: ASP.NET
X-FEServer: AM0PR06CA0096
WWW-Authenticate: Basic Realm="",Negotiate
Date: Fri, 31 Jan 2020 13:02:46 GMT
Connection: close

--snip--
```

#### Nonexistent Account

The request below contains the following Base64 encoded credentials in the Authorization header: [email protected]:Password1

```
OPTIONS /Microsoft-Server-ActiveSync HTTP/1.1
Host: outlook.office365.com
Connection: close
MS-ASProtocolVersion: 14.0
Content-Length: 2
Authorization: Basic aW52YWxpZF91c2VyQGNvbnRvc28uY29tOlBhc3N3b3JkMQ==
```

This elicits the following response ("401 Unauthorized" but this time without the `X-MailboxGuid` header, indicating the username is invalid.

```
HTTP/1.1 401 Unauthorized
Content-Length: 1293
Content-Type: text/html
Server: Microsoft-IIS/10.0
request-id: 2944dbfc-8a1e-4759-a8a2-e4568950601d
X-CalculatedFETarget: DB3PR0102CU001.internal.outlook.com
X-BackEndHttpStatus: 401
WWW-Authenticate: Basic Realm="",Negotiate
X-FEProxyInfo: DB3PR0102CA0017.EURPRD01.PROD.EXCHANGELABS.COM
X-CalculatedBETarget: DB7PR04MB5452.eurprd04.prod.outlook.com
X-BackEndHttpStatus: 401
X-RUM-Validated: 1
X-DiagInfo: DB7PR04MB5452
X-BEServer: DB7PR04MB5452
X-Proxy-RoutingCorrectness: 1
X-Proxy-BackendServerStatus: 401
X-FEServer: DB3PR0102CA0017
X-Powered-By: ASP.NET
X-FEServer: AM0PR04CA0024
Date: Fri, 31 Jan 2020 16:19:11 GMT
Connection: close

--snip--
```

### Autodiscover Enumeration

The autodiscover endpoint allows for user enumeration without an authentication attempt. The endpoint returns a 200 status code if the user exists and a 302 if the user does not exists (unless the redirection is made to an on-premise Exchange server).

#### Existing User

```
GET /autodiscover/autodiscover.json/v1.0/[email protected]?Protocol=Autodiscoverv1 HTTP/1.1
Host: outlook.office365.com
User-Agent: Microsoft Office/16.0 (Windows NT 10.0; Microsoft Outlook 16.0.12026; Pro
Accept-Encoding: gzip, deflate
Accept: */*
Connection: close
MS-ASProtocolVersion: 14.0
```

```
HTTP/1.1 200 OK
Cache-Control: private
Content-Length: 97
Content-Type: application/json; charset=utf-8
Vary: Accept-Encoding
Server: Microsoft-IIS/10.0
request-id: fee7f899-7115-43da-9d34-d3ee19920a89
X-CalculatedBETarget: AM0PR09MB2882.eurprd09.prod.outlook.com
X-BackEndHttpStatus: 200
X-RUM-Validated: 1
X-AspNet-Version: 4.0.30319
X-DiagInfo: AM0PR09MB2882
X-BEServer: AM0PR09MB2882
X-Proxy-RoutingCorrectness: 1
X-Proxy-BackendServerStatus: 200
X-Powered-By: ASP.NET
X-FEServer: AM0PR0202CA0008
Date: Mon, 02 Mar 2020 12:50:48 GMT
Connection: close

{"Protocol":"Autodiscoverv1","Url":"https://outlook.office365.com/autodiscover/autodiscover.xml"}
```

#### Nonexistent User

```
HTTP/1.1 302 Found
Cache-Control: private
Content-Length: 277
Content-Type: text/html; charset=utf-8
Location: https://outlook.office365.com/autodiscover/autodiscover.json?Email=nonexistent%40contoso.com&Protocol=Autodiscoverv1&RedirectCount=1
Server: Microsoft-IIS/10.0
request-id: 1c50adeb-53ac-41b9-9c34-7045cffbae45
X-CalculatedBETarget: DB6PR0202MB2568.eurprd02.prod.outlook.com
X-BackEndHttpStatus: 302
X-RUM-Validated: 1
X-AspNet-Version: 4.0.30319
X-DiagInfo: DB6PR0202MB2568
X-BEServer: DB6PR0202MB2568
X-Proxy-RoutingCorrectness: 1
X-Proxy-BackendServerStatus: 302
X-Powered-By: ASP.NET
X-FEServer: AM0PR0202CA0013
Date: Mon, 02 Mar 2020 12:50:50 GMT
Connection: close

Object moved

Object moved to here.

```

### Office.com Enumeration

**WARNING**: This method only works for organization that are subscribers of Exchange Online and that do not have on-premise or hybrid deployment of Exchange server.

For companies that use on premise Exchange servers or some hybrid deployment and based on some configuration I haven't identified yet, the server might return a value indicating the username exists for any username value.

The method is useful when you don't want to burn an authentication attempt with 'Password1' :)

#### Determining if a user exists

The IfExistsResult property is used to describe if and how an account exists. As discussed on this [RSM blog article](https://warroom.rsmus.com/enumerating-emails-via-office-com/), the values are as follows:

| Item | Price |
|--------------|-----------|
| -1 | An unknown error |
| 0 | The account exists, and uses that domain for authentication |
| 1 | The account doesn’t exist |
| 2 | The response is being throttled |
| 4 | Some server error |
| 5 | The account exists, but is set up to authenticate with a different identity provider. This could indicate the account is only used as a personal account |
| 6 | The account exists, and is set up to use both the domain and a different identity provider |

##### Existing User

When the account exists, `IfExistsResult` is set to one of the integers mentioned above, commonly `1`.

```
POST /common/GetCredentialType?mkt=en-US HTTP/1.1
Host: login.microsoftonline.com
Accept-Encoding: gzip, deflate
User-Agent: Mozilla/5.0 (X11; Linux x86_64) AppleWebKit/537.36 (KHTML, like Gecko) Chrome/79.0.3945.88 Safari/537.36
Accept: application/json
Connection: close
client-request-id: 4345a7b9-9a63-4910-a426-35363201d503
hpgrequestid: 23975ac9-f51c-443a-8318-db006fd83100
Referer: https://login.microsoftonline.com/common/oauth2/authorize
canary: --snip--
hpgact: 1800
hpgid: 1104
Origin: https://login.microsoftonline.com
Cookie: --snip--
Content-Length: 1255
Content-Type: application/json

{
"checkPhones": false,
"isOtherIdpSupported": true,
"isRemoteNGCSupported": true,
"federationFlags": 0,
"isCookieBannerShown": false,
"isRemoteConnectSupported": false,
"isSignup": false,
"originalRequest": "rQIIA--snip--YWSO2",
"isAccessPassSupported": true,
"isFidoSupported": false,
"isExternalFederationDisallowed": false,
"username": "[email protected]",
"forceotclogin": false
}
```

```
HTTP/1.1 200 OK
Cache-Control: no-cache, no-store
Pragma: no-cache
Content-Type: application/json; charset=utf-8
Expires: -1
Strict-Transport-Security: max-age=31536000; includeSubDomains
X-Content-Type-Options: nosniff
client-request-id: 177110da-7ce4-4880-b856-be6326078046
x-ms-request-id: c708b83f-4167-4b4c-a1db-d2011ecb3200
x-ms-ests-server: 2.1.9966.8 - AMS2 ProdSlices
Referrer-Policy: strict-origin-when-cross-origin
P3P: CP="DSP CUR OTPi IND OTRi ONL FIN"
Set-Cookie: fpc=ArU-Dva0f59Eg4t_V3VsX_TsYIXWAQAAAFRGxtUOAAAA; expires=Sun, 01-Mar-2020 16:01:26 GMT; path=/; secure; HttpOnly; SameSite=None
Set-Cookie: x-ms-gateway-slice=prod; path=/; SameSite=None; secure; HttpOnly
Set-Cookie: stsservicecookie=ests; path=/; secure; HttpOnly; SameSite=None
Date: Fri, 31 Jan 2020 16:01:26 GMT
Connection: close
Content-Length: 587

{
"Username":"[email protected]",
"Display":"[email protected]",
"IfExistsResult":0,
"ThrottleStatus":0,
"Credentials":{
"PrefCredential":1,
"HasPassword":true,
"RemoteNgcParams":null,
"FidoParams":null,
"SasParams":null
},
"EstsProperties":{
"UserTenantBranding":null,
"DomainType":3
},
"IsSignupDisallowed":true,
"apiCanary":"--snip--"
}
```

##### Nonexistent User

When the account does not exist, `IfExistsResult` is set to 1.

```
HTTP/1.1 200 OK
Cache-Control: no-cache, no-store
Pragma: no-cache
Content-Type: application/json; charset=utf-8
Expires: -1
Strict-Transport-Security: max-age=31536000; includeSubDomains
X-Content-Type-Options: nosniff
client-request-id: 95bba645-c3b0-4566-b0f4-237bd3df2ca7
x-ms-request-id: fea01b74-7a60-4142-a54d-7aa8f6471c00
x-ms-ests-server: 2.1.9987.14 - WEULR2 ProdSlices
Referrer-Policy: strict-origin-when-cross-origin
P3P: CP="DSP CUR OTPi IND OTRi ONL FIN"
Set-Cookie: fpc=Ai0TKYuyz3BCp7OL29pUnG7sYIXWAQAAABsDztUOAAAA; expires=Sat, 07-Mar-2020 12:57:44 GMT; path=/; secure; HttpOnly; SameSite=None
Set-Cookie: x-ms-gateway-slice=estsfd; path=/; SameSite=None; secure; HttpOnly
Set-Cookie: stsservicecookie=ests; path=/; secure; HttpOnly; SameSite=None
Date: Thu, 06 Feb 2020 12:57:43 GMT
Connection: close
Content-Length: 579

{
"ThrottleStatus": 0,
"apiCanary": "--snip--",
"Username": "[email protected]",
"IfExistsResult": 1,
"EstsProperties": {
"UserTenantBranding": null,
"DomainType": 3
},
"Credentials": {
"PrefCredential": 1,
"FidoParams": null,
"RemoteNgcParams": null,
"SasParams": null,
"HasPassword": true
},
"IsSignupDisallowed": true,
"Display": "[email protected]"
}
```

## Contributors

* [@jenic](https://github.com/jenic) - Arguments parsing and false negative reduction.
* [@Mike-Crowley](https://github.com/Mike-Crowley) - IfExistsResult description correction.