I’m starting to get lots of questions about how to determine when exactly an Office 365 account was compromised. Typically, the two most common compromises are phishing and weak passwords. This article is going to focus on one of the ways weak passwords are exploited.

The first thing to appreciate here is that, generally, Office 365 won’t maintain logs needed for detailed investigation beyond 7 days and secondly most logging in Office 365 is disabled by default. There are a number of different audits in the product that you should enable, the major one is Activity auditing which I have detailed how to enable here:

Enable activity auditing in Office 365

The place I suggest you start any investigation is with my free PowerShell Office 365 user login auditing script which I have detailed here:

Auditing Office 365 logins via PowerShell

If you are a CIAOPS Patron subscriber I have an enhanced version of this same script that also outputs the results to a CSV file.

The above shows you the screen output of this script. You’ll see successful logins in green and unsuccessful ones in red.

The indication that an account has been compromised will either be:

1. Successful login from a suspicious IP address (indicating phishing and the fact that the bad actors already have the user’s password)

or

2. A number of failed logins to an account followed immediately by a successful login (indicating that the account password has been guessed via brute force).

In this article I’m going to focus on hunting down item 2, as item 1 is tougher, and means combing through IP addresses.

So, what we now need to do is take a look at the CSV file the script generated and see if we can find the login pattern we are looking for.

I’m using Excel as my primary investigation tool here as it provides more flexibility than other tools for me.

Firstly, I’m going to insert a table to make querying data easier.

Next, I’m going to filter out my know corporate IP addresses so I am only left with those I don’t recognise. In this case, I’m also going to only focus on a single user. Finally, I’m going to sort the times from newest to oldest.

Now what I’m going to do is hone in on an unfamiliar IP – in this case 110.82.6.244. When I filter the file further I find over 85 entries for that IP as shown above. The interesting things is that these entries happen sequentially on the same day and start at 1:16AM and end at 1:35AM. This confirms that my account has probably been the subject of some sort of automated ‘password spray’ attack. This basically means the bad actors have used an automated process to repeatedly try to login to my account using different passwords.

What passwords are they using? There are huge tables out there with all sorts of passwords people like to use. Where did these tables come from? Typically from systems that have been compromised and had all their login credentials stolen. These stolen credentials are now being re-purposed sand used to attack other accounts. Have a look at Troy Hunt’s site:

Have I been Pwned?

if you haven’t already to get an idea of the sheer volume of credentials there are in the wild.

You’ll note that in this list I don’t have any filter on the Operation column. Why? Because, I’m look for the pattern of repeated logins failures and THEN a successful login indicating that the account password has been guessed.

Luckily, for this attack IP address I don’t see that pattern. So basically, they tried 85 different attempts over a 20 minutes or so and don’t appear to have gained access. Phew.

When I do a lookup on the location of this IP address, I find it is in China.

I can do some more investigation by digging into the user account details in the Azure Active Directory service inside the Azure portal as shown above.

Basically I’ve gone into the Azure portal, selected the Azure Active Directory service then select Users and then the specific user I want to to investigate.

From the items that appear on the left for that specific user I select Sign-ins and then customise the search so that:

Application = Office 365 Exchange

Status = Failure

You then need to select the Apply button to update the query. Once I have done this I now get a list of login failures as you can see above.

If I select an entry in question (i.e. one from the previous results in the CSV file generated by my script) I see the above details.

The details show it is from the same IP address (110.82.6.244) and that client app in question was SMTP, i.e. the login was attempting to do an email account login.

It is also interesting to note that Microsoft blocked the attack by locking the account because it tried to login in too many times. Thus, Microsoft is detecting this common sort of attack and mitigating it based in the IP address and the repeated attempts from a single IP address. Thanks Microsoft.

You can click through the remaining links at the top of the page to get other information.

Unsurprisingly, there is no device info as you can see above.

This screen also gives you the option to download this log information to a CSV directly from the Azure portal for further analysis if you want. Down side is, that it is simply the single user you see here, not across all the users in the tenant.

Now that tenant wide option is available if you return to the top level options for Azure Active Directory, but you’ll need to have a subscription for Azure AD Premium P1 or better.

What I have therefore shown you so far will work with any Office 365 tenant and that is probably a good place to call and end to this particular article. I’ll be doing more around additional investigation options available in both standard and premium offerings soon, but for now I’ll leave you with an article from Microsoft that everyone managing an Office 365 environment should read:

Azure AD and ADFS best practices: defending against password spray attacks

and watch out for more from me around detecting and blunting attacks on Office 365.

YOUR call to action after reading all this should be to go and check your tenant for attacks like this and ensure you are doing everything you can to prevent their possible success.

Data Loss Prevention (DLP) is typically an outbound scanning technology in Office 365 that monitors and prevents sensitive information from leaving the organisation.

Previous, DLP was only part of Exchange Online. It is still possible to configure policies only in Exchange Online as you can see above, in the Exchange Online Admin console.

To do this in PowerShell you’d use the command:

new-dlppolicy

The new of way doing DLP in Office 365 is via the Security and Compliance Center as you see above. The benefits of using this new method is that it is possible to use policies to not only protect Exchange Online but SharePoint and OneDrive for Business from data leakage.

Office 365 DLP has a number of pre-canned policy templates you can use as shown above. It is always best practices to at least start with these since they cover the basics.

You’ll note above that I’m looking to configure a policy based on Australian Financial Data. This in effects scans material looking for SWIFT code, Australia Tax File Number, Australia Bank Account Number and Credit Card as you see in the lower right.

Proceeding with the GUI wizard then asks for the areas in Office 365 to protect. As you can see from the above, these locations include Exchange email, SharePoint sites and OneDrive accounts. You can modify the inclusion and exclusions to all these different areas if you wish.

You then determine what content you are looking for in the policy settings, as well as when to detect.

You can customise these rules if you wish, as shown above.

Finally, you can determine how this policy will operate and whether it is active.

Why is all this important for using PowerShell? The simple answer is, that with many options, knowing what everything does in the web interface is going to help when it comes to implementing via PowerShell.

So, to start the PowerShell configuration process you are going to need to connect to the Office 365 Security and Compliance center using PowerShell. You’ll find scripts to do that at my GitHub repo here:

https://github.com/directorcia/Office365

We don’t want to use the older, Exchange Online only cmdlets like:

new-dlppolicy

we’ll be using the newer Security and Compliance cmdlets like

new-dlpcompliancepolicy

The first thing I need to is create a new DLP policy called ‘Australian Privacy Act’ and do that with the commands:

$params = @{
‘Name’ = ‘Australian Privacy Act’;
‘ExchangeLocation’ =’All’;
‘OneDriveLocation’ = ‘All’;
‘SharePointLocation’ = ‘All’;
‘Mode’ = ‘Enable’
}
new-dlpcompliancepolicy @params

Now, this basically establishes the policy and the location that it applies to in Office 365. There are not any rules yet to check the content.

To do this. you need to create a variable that holds the sensitive data types you want to check. Yo can do that with the following:

$senstiveinfo = @(@{Name =”Australia Driver’s License Number”; minCount = “1”},@{Name =”Australia Passport Number”;minCount=”1″})

You’ll find information about the specific sensitive data types for you region here:

https://docs.microsoft.com/en-us/exchange/policy-and-compliance/data-loss-prevention/sensitive-information-types?view=exchserver-2019

With all that in place, the rule can be added to the existing policy using the following:

$Rulevalue = @{
‘Name’ = ‘Low volume of content detected Australia Privacy Act’;
‘Comment’ = “Helps detect the presence of information commonly considered to be subject to the privacy act in Australia, like driver’s license and passport number.”;
‘Policy’ = ‘Australian Privacy Act’;
‘ContentContainsSensitiveInformation’=$senstiveinfo;
‘BlockAccess’ = $true;
‘AccessScope’=’NotInOrganization’;
‘BlockAccessScope’=’All’;
‘Disabled’=$false;
‘GenerateAlert’=’SiteAdmin’;
‘GenerateIncidentReport’=’SiteAdmin’;
‘IncidentReportContent’=’All’;
‘NotifyAllowOverride’=’FalsePositive,WithJustification’;
‘NotifyUser’=’Owner’,’SiteAdmin’,’LastModifer’
}

New-dlpcompliancerule @rulevalue

You should recognise many of these settings from what is in the web interface. Don’t forget that DLP takes a while to crawl through all the different content areas you have selected and be applied.

If all of that executes successfully, then you should see a new DLP policy in the web interface as shown above.

If you have an Office 365 or Microsoft 365 licenses that includes DLP, you should use the pre-existing templates that Microsoft provides you for you region and create a new policy for each.

You can, of course, customise these easily by changing the PowerShell parameters or creating your own rules to suit. The great thing is, once you have worked all of this out you now a configuration you can apply to every tenant quickly and easily.

That is the power of automation thanks to PowerShell!