User Enumeration Part 2 – Microsoft Office 365

By Mike Saunders | March 10, 2020

It’s not uncommon on external pen tests and red team engagements to find very little attack surface on the customer’s internet-facing networks. Customers have started shifting services to cloud providers, making it harder to find targets. This blog describes how to enumerate users within the Microsoft O365 ecosystem.

Part 1 of this series is located here: http://www.redsiege.com/blog/2020/01/user-enumeration-part-1-building-name-lists/

O365 Login Page

We can use the login portal at https://login.microsoftonline.com to determine if our customer has services hosted within the Microsoft ecosystem. If the company does not have any resources hosted with MS, when we attempt to log in with a any email address for their domain, we’ll receive the following error:

Domain not hosted with MS Domain Not Hosted In MS

 

If the customer does have resources within the Microsoft ecosystem, there are several different responses we may encounter. If we provide an invalid email address, we’ll receive an error similar to the following.:

Valid domain but Bad User Invalid Email Address

If we have provided a valid email, one of two things may occur. The customer may be using the default O365 login page, in which case you’ll be prompted to enter in the user’s password.

Password Prompt Password Prompt for Valid Email Address[/caption]

Some customers may be using their own login portal, or using a 3rd party MFA solution, in which case you will be redirected to a different site and will see a message similar to the following.

Redirection to Custom Login Page Redirection to Organization Sign-In Page[/caption]

Automated Enumeration

Being able to manually tell if a company has resources in O365 is a great first step. Since this blog is about user enumeration, we likely want to do this in an automated fashion. The normal O365 login POST request contains a lot of headers and parameters, but we can strip out almost everything, leaving the following bare-bones request:

Login POST Request Login POST Request

The server will respond with a 200 OK response containing JSON data. The specific component of the response we’re looking for is the IfExistsResult value. If the value is 1, the specified email address does not exist within the organization.

Invalid Email Address Invalid Email Address

There are a number of blogs written about O365 user enumeration, and there are tools written to do enumeration. All of the ones I’ve seen are missing information about the IfExistsResult value, which could lead you to not identifying valid users. These blogs and tools look for an IfExistsResult value of 0 to determine if the username is valid. There are two additional codes, however, which also indicate a valid user – 5 and 6. I found this script on Github which seems to indicate the user’s email address has also been set up to use personal services, which will result in a prompt asking if this is a work or personal account. However, I haven’t been able to find other resources to confirm that this is indeed the nature of response values 5 and 6.

I typically use Burp Pro’s Intruder module to automate testing. Setting up grep match rules for the various ifExistsResult codes allows me to quickly see which addresses are valid To wrap it all up, the following table summarizes validIfExistsResult result codes.

IfExistsResult Meaning
0 Valid Email Address
1 Invalid Email Address /
Domain Not Hosted in O365
5 Valid Email Address
6 Valid Email Address

Moving beyond T4 – Deconstructing Nmap Tuning

By Red Siege | July 6, 2022

by Alex Norman, Senior Security Consultant Nmap -T4 -iL targets.txt This is a very common scan string that many people use to get initial recon done on assessments and, to […]

Learn More
Moving beyond T4 – Deconstructing Nmap Tuning

Creating a Simple Windows Domain for Offensive Testing: Part 4

By Red Siege | June 23, 2022

By: Justin Palk, Security Consultant This is part four of my series of blog posts on creating a windows domain for offensive security testing. In part 1, I stood up […]

Learn More
Creating a Simple Windows Domain for Offensive Testing: Part 4

Creating a Simple Windows Domain for Offensive Testing: Part 3

By Red Siege | June 15, 2022

by Security Consultant Justin Palk Welcome back to my series on setting up a Windows domain for offensive testing. In the first two installments (Part 1, Part 2), I stood […]

Learn More
Creating a Simple Windows Domain for Offensive Testing: Part 3

Find Out What’s Next

Stay in the loop with our upcoming events.