Msmailprobe - Office 365 And Exchange Enumeration - Hacking Land

Office 365 and Exchange Enumeration

It is widely known that OWA (Outlook Webapp) is vulnerable to time-based user enumeration attacks. This tool leverages all known, and even some lesser-known services exposed by default Exchange installations to enumerate users. It also targets Office 365 for error-based user enumeration.

Getting Started

If you want to download and compile the simple, non-dependant code, you must first install GoLang! I will let the incredible documentation, and other online resources help you with this task.

https://golang.org/doc/install

You may also download the compiled release here.

Syntax

List examples of commands for this applications, but simply running the binary with the examples command:

./msmailprobe examples

You can also get more specific help by running the binary with the arguments you are interested in:

./msmailprobe identify./msmailprobe userenum./msmailprobe userenum --onprem./msmailprobe userenum --o365

Usage

Identify Command

Used for gathering information about a host that may be pointed towards an Exchange or o365 tied domain
Queries for specific DNS records related to Office 365 integration
Attempts to extract internal domain name for onprem instance of Exchange
Identifies services vulnerable to time-based user enumeration for onprem Exchange
Lists password-sprayable services exposed for onprem Exchange host

Flag to use:	-t to specify target hostExample:	./msmailprobe identify -t mail.target.com

Userenum (o365) Command

Error-based user enumeration for Office 365 integrated email addresses

Flags to use:	-E for email list OR -e for single email address	-o [optional]to specify an out file for valid emails identified	--threads [optional] for setting amount of requests to be made concurrentlyExamples:	./msmailprobe userenum --o365 -E emailList.txt -o validemails.txt --threads 25	./msmailprobe userenum --o365 -e [email protected]

Userenum (onprem) Command

Time-based user enumeration against multiple onprem Exchange services

Flags to use:	-t to specify target host	-U for user list OR -u for single username	-o [optional]to specify an out file for valid users identified	--threads [optional] for setting amount of requests to be made concurrentlyExamples:	./msmailprobe userenum --onprem -t mail.target.com -U userList.txt -o validusers.txt --threads 25	./msmailprobe userenum --onprem -t mail.target.com -u admin

Acknowledgments

poptart - For a truck load of golang assistance, poking of Exchange services, and help testing timing of responses
jlarose - Parsing decimal data within NTLMSSP authentication reponse for internal domain name
Vincent Yui - Office 365 check python script
grimhacker - Discovery/disclosure of error-based user enumeration within Office 365 blog post
Nate Power - Discovery and disclosure of OWA time-based user enumeration