Investigating an Office 365 account compromise

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)


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 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 ( 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.

Office 365 services PowerShell bulk connection script

I spend a lot of my time logging in and out of various tenants using PowerShell. Some tenants require Multi Factor Authentication (MFA), others don’t. Sometimes I need to just use SharePoint Online or maybe Exchange and Teams.

Already having all the appropriate online services connection scripts in my Github repo here:

I wanted a way to make it easy for me to login to any tenant, MFA or not, as well as an service, or combination of services. Thus my latest script at:

provides a neat solution I believe.

They way it works is that:

1. You need to copy all the files from my Github repo to a directory on your local environment.

2. Execute the o365-connect-bulk.ps1 script where all the scripts are with following command line options:

-mfa if MFA required for login

-std if Microsoft Online connect required

-aad if Azure AD connect required

-exo if Exchange Online connect required

-s4b if Skype for Business Online connect required

-sac if Security and Compliance Center connect required

-spo if SharePoint Online connect required

-tms if Microsoft Teams connect required

-aadrm if Azure AD Rights Management connect required

You can combine some or all of these onto the command line like so:

.\o365-connect-bulk.ps1 –mfa –exo –tms

which will do a login with MFA for Exchange Online and Microsoft Teams. Or:

.\o365-connect-bulk.ps1 –std –spo

which will login with no MFA to Microsoft Online and SharePoint Online.

The way that I use scripts is to break them down into small scripts. I don’t like the idea of large ‘mega’ scripts that do everything because they are harder to maintain and when they break they are harder to debug. This way, o365-connect-bulk.ps1 relies in the other stand alone scripts in the same directory which it calls as needed.

The down side to this approach is that you may need to login to the tenant multiple times as each independent script runs. That is only initially and a small price to pay for the added flexibility and functionality I would suggest.

If need to login to many different tenants and services throughout the day then this bulk connection script should help you.

Configuring Office 365 DLP with PowerShell

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:



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:

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


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


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:

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’;
‘BlockAccess’ = $true;

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!

Microsoft Cloud service descriptions


One of the common pain points that people are reporting in my recent Challenges with Microsoft Cloud survey here:

What is you biggest challenge with the Microsoft Cloud

is wanting a single location that compares all of the offerings side by side.

Unfortunately, given the huge number of options across different teams in Microsoft there really isn’t a single place. This stems back to an earlier article I wrote about

Why IT today is like coffee

which in short details how we live in a world were people want lots of choices rather than a single monolithic solution. This is so people can get EXACTLY what they want and not have to pay for things they don’t want or need. The price we pay for lots of choice is, lots of choice.

All is not lost however because there are few places you can go to get a pretty good overview what the Microsoft Cloud offers.

The first place to start is the Office 365 service descriptions. This will lay out in great detail all the plans side by side and features that each include. You can drill down beyond the suites into individual service like Exchange and SharePoint Online if you want.

Now for Azure the best option is probably Products by region. This will show you each Azure service as well the region that it is available in. To get an idea of all the abilities of Azure have a look at the list of Azure products as a reference guide.

If you are interested in what Microsoft 365 Business contains then look at the Microsoft 365 Business Service Description.

Of course, much of this gets updated regularly so how can you keep up with changes? Well, use the Recent services description changes to see what’s new in Office 365. There is also the new and updated Microsoft 365 Roadmap, which will help you plan what changes are down the pipe.

Azure has something similar over at Azure updates.

Many of these update locations have the ability for you to subscribe to via RSS or email so you can get prompted when things change. I have detailed previous how you can use Microsoft Teams, Office 365 and Yammer to stay up to date by pushing the change feeds into these services automatically.

With lots of options comes lots of detailed information. It is simply a fact of life these days. I would suggest that the services descriptions should be the source of truth for what is included in Office 365 and Microsoft 365. Everything else I have seen is a summary of this. Azure is a different kind of beast, so start with the list of Azure products and drill in from there.

Remember, as Clay Shirky says, it isn’t information overload, it is filter failure. You can’t ingest everything, so find the best stuff and consume that. Be selective with your information sources and always search for the highest quality. Hopefully, I’ve given you some quality places to start here.

What is your biggest challenge with the Microsoft Cloud


Tis the season for a survey I think. What I’d like to do is start off with this one question:

What is the biggest challenge you face with the Microsoft Cloud?

That’s it. Just one question. You can answer the question here:

I’ll collate all the answers and report back on the results. I’ll try and group the issues into categories so you get a better of idea of what generally are the major challenges a majority of people have.

It doesn’t matter whether you are an end user, business, IT resellers, IT professional, whatever, please take a moment to share what you find most challenging about the Microsoft Cloud (Office 365, Microsoft 365, Azure, etc)

The more people that take a moment to answer the more results and information we’ll have to share. The results are anonymous.

Thanks in advance for completing the survey.

Need to Know podcast–Episode 197

In this episode we focus on security starting with our interview of Alex Wilson from Yubico talking all about multi factor authentication. We take the time to dive deep into the benefits of using devices like the Yubikey to protect identities an help prevent phishing attacks. Brenton and I also discuss a number of interesting security items before the interview as well as give you the latest updates from the Microsoft Cloud.

Take a listen and let us know what you think –

You can listen directly to this episode at:

Subscribe via iTunes at:

The podcast is also available on Stitcher at:

Don’t forget to give the show a rating as well as send us any feedback or suggestions you may have for the show.


Alex Wilson –




Join us for the 200th episode

Australia gets world-first encryption busting laws

Australia passes new law to thwart strong encryption

Microsoft adopts ethical principles aiming to bar misuse of facial recognition technology

New breakthrough in combating tech support scams

Mastercard and Microsoft join forces to Advance Digital Identity Innovations

New Office app icons

Outlook on iOS gets a redesign

CIAOPS Patron program

Unable to save attachments to SharePoint Online

One of the most important things when you implement adoption is to have a positive initial experience. This typically means ‘easing’ a user’s transition during the adoption process. If too many things are different, then there is much more likely to be a negative impression of the new processes. This slows adoption and at worst, can actually halt it in its tracks.

When moving to Microsoft 365, one of the most common things that a user needs to accomplish to be able to save and add attachments to emails. They have been performing this seamlessly using on premises file servers for years. They simply select to attach and then navigate to the file, attach it, then send. Easy.

Unfortunately, as I have documented before:

Saving attachments to SharePoint

it isn’t easily done with SharePoint Online. This is really strange, given that SharePoint Online is the place where users should save and access common files in the Microsoft Cloud. Let’s take a look at the issues I’m taking about.


So an email arrives in my inbox on Outlook on the desktop, as shown above.


I want to upload this directly into an existing SharePoint stand alone Team Site, but as you can see the only option I have is my own personal OneDrive for Business or a range of Office 365 Groups and Teams that already exist.

Just to make sure I haven’t missed anything, I’ll select the More option at the bottom of the list.


Now I only have the option to save to a Group (which includes Microsoft Teams). So, let’s say I select the Sales Group (which is actually a Microsoft Team).

I’m now returned to Outlook. Where did that attachment actually go?


So, if I call up my Sales Team and rifle through all the file locations in Teams interface, I can’t find the file as you see above!


Turns out that the attachment I saved is placed into the root of the default Document Library in the Microsoft Team as you see above. But guess what? There is no way to actually see that unless I navigate to that location via SharePoint. I actually can’t see that attachment I just saved if I’m using the Microsoft Teams app! They all end up in the root of the Documents location, which isn’t accessible in the Teams app!


This means, that the only REAL solution for users to save the document to other locations in various SharePoint Document Libraries, is to firstly sync those destination locations to their desktop and then save the attachments the old fashioned way to the sync location so they will end up in SharePoint.

That means, to save or add attachments I firstly have to sync EVERY location I might want to save a file too!


Outlook Web Access is actually worse than the desktop client as the only options you have are to download or save to OneDrive for Business as seen above.


Interestingly, if I want to attach a file from a SharePoint site I can navigate to Browse Web Locations, select the Team Site I want


and I see a Windows Explorer pane where I can navigate to locate the file I wish to attach, just like on premises days. However, the look and feel here is pretty dated and requires Windows Explorer to be working and may pop up warning dialogs which will freak most users out.


When I use Outlook Web Access I can Browse cloud locations for an attachment


I effectively only see my OneDrive for Business as shown above.

These experiences leave a bad taste in the mouth for users, especially first time users grasping with the ‘modern’ way of working. They need to have an experience which is pretty much identical to the one they had on premises. Why can’t we simply save and add attachments directly from SharePoint Online Team Sites like we have always been able to do from on premises network file shares?

I’m seeing this end user frustration more and more in the field and was prompted to write the article to hopefully rally the masses to get a change enacted. So the best thing you can do is visit this UserVoice request:

and vote it up.

Next, tweet about getting this enabled to the following accounts:


I will be!

Perhaps I’m missing something obvious here and if I am please let me know but I don’t think I am. Help me raise awareness and improve Outlook so it is easier for users to adopt Microsoft 365!