Office 365’s MFA is vulnerable to EvilGinx2

According to the latest Microsoft Security Intelligence Report, spear phishing remains the preferred attack method used by hackers. Microsoft detected a 250% increase in phishing messages between January and December 2018.

Figure 1 Page 21 of the Microsoft Security Intelligence Report Volume 24

Many organizations have deployed 2FA as a layer of defense to guard against phishing, so that if the user gives away the username and password, the attacker shouldn’t be able to logon to the user account. The purpose of this blog post is to raise awareness that Office 365 in particular is now vulnerable to “network session hijacking proxy theft” which allows an attacker to sign in regardless of the MFA solution (MSFT, Duo, RSA, SMS, etc). The authentication token is captured after the victim is tricked to going to a credential stealing website where they perform MFA through a proxy server. The token is then re-played by the attacker who can sign in as the user.

To see a demonstration of this, watch this Youtube video, https://www.youtube.com/watch?v=k4bq5A-icBw (Credit to @thehappydinoa)

Prior to this video, I haven’t been able to find any evidence of blog posts or videos demonstrating a successful bypass against Office 365’s 2FA capabilities. It’s worth noting that Office 365 is not unique – the same man-in-the-middle attack works against Google, LinkedIN, and other platforms as first demonstrated by Kevin Mitnick (KnowBe4) in May 2018 (original blog post (here). Since then other phishlets have been developed for Amazon, Github, Protonmail, Citrix, OKTA, Twitter, Instagram, Facebook, reddit, and consumer Outlook.com, and now Office 365.

The reason why this is important is because much of the security industry emphasizes MFA without raising awareness of this man-in-the-middle threat. For example, in my opinion one of the best presentations at the 2018 RSA conference was given by Booz | Allen | Hamilton which gave overwhelming evidence that 2FA would have stopped or reduced the impact of every one of the 159,700 total cyber incidents reported by the Online Threat Alliance in 2017. (Page 6, reference here). Now, the caveat has to be added that MFA would have stopped cyber incidents as long as victims were not tricked to going to proxy websites.

We have taken for granted that the very best anti-spam/anti-phish security solutions will not block 100% of the threats, and it is now time we accept the reality that MFA will not always prevent unauthorized authentication (much like how the SMS version of 2FA is no longer recommended or sufficient).

Roger Grimes of KnowBe4 gave a wildly popular presentation at the 2019 RSA Security Conference (requiring overflow seating) which listed 12 methods to bypass MFA (PDF download here). Some of these techniques require the attacker to invest a lot of time and sometimes money and risk (sim swapping) or be adept at social engineering (phone number porting). However, this all changed when Kuba Gretzky (@mrgretzky) released EvilGinx in 2017. Kuba showed how attackers can reduce their risk, cost, and effort through “network session hijacking proxy theft.” Grimes mentioned this technique among the 12 MFA bypass methods in his RSA presentation, and included a video showing how Kuba’s updated EvilGinx2, successfully bypasses the 2FA of Gmail and LinkedIN. At that time, there was no Office 365 phishlet available, but it was later added by @JamesCullum. 

In January at a Microsoft event, I asked Microsoft if Office 365 defended or detected network session hijacking proxy theft, specifically EvilGinx2. They stated that Office 365 would prevent this technique.

Enter Aidan Holland (@thehappydinoa), who recently verified that EvilGinx2 can successfully bypass Office 365’s 2FA. Aidan also solved a vexing problem for Troy Hunt, who was trying to get a list of the Fortune 500 for his security research. Read about his solution to solve that problem here.

Aidan’s video is the first showing a successful bypass of Office 365 MFA:

https://www.youtube.com/watch?v=k4bq5A-icBw

(Credit to @thehappydinoa)

It’s worth noting that the phishing link generated by EvilGinx2 is not blocked by MSFT EOP, Office ATP, Microsoft Defender ATP, or Windows Defender SmartScreen.

In the next blog post, I will discuss ways to protect against EvilGinx2.

Analysis of DNS Recon of the Fortune 500 (Part 1 of 3)

In this three-part blog series, I will be writing about interesting trends amongst the Fortune 500 using public DNS reconnaissance posted in open source github repositories. This first post is focused on the email security providers used by the Fortune 500. The other posts will analyze adoption trends in DMARC and IdP Federation.

One of the favorite people I follow on twitter is Daniel Streefkerk (@dstreefkerk) from Sydney, Australia. Daniel tweeted on February 11th about a script he published to github (here) that performs DNS reconnaissance He posted a graph (here) of which email security providers were used by the top 250 Australian Companies.

 

Then a few days later he posted (here) how he updated the script to check for federation information (ex: Does the domain federate with OKTA, ADFS, Ping, OneLogin, etc?) and other interesting things like whether Office 365 was detected, the tenant name discovered (typically it is publicly listed in the DKIM DNS record).

I was curious how his findings in Australia compared to companies in the United States, but I couldn’t think of a simple way of finding the fortune 500 email domain names. Turns out, I was not alone. One of Daniel’s fellow Auzzies, Troy Hunt, a Microsoft Regional Director (a title similar to an MVP) recently asked a similar question (here) on March 31st:

Everyone seemed to have ideas but Troy seemed frustrated at one point that there wasn’t a simple list available somewhere. That’s when Aidan Holland (@thehappydinoa) came to the rescue and wrote an elegant 152-line python script (here) to gather about 455 of the 500 from a JSON query against hifld data. He then took that data and queried virus total, threat crowd, crt.sh, and finally validated it was a valid DNS domain for email by querying the MX record in DNS. All in 152 lines of Python. Impressive.

His JSON query the initial data set came from ARCGIS.COM with this code:

FORTUNE_500_JSON
=
“https://opendata.arcgis.com/datasets/a4d813c396934fc09d0b801a0c491852_0.geojson”


Aidan published the resulting list of 455 domain names (here). Then using PowerShell, we can pipe that into Daniel’s DNS recon script, to produce a report showing the email filtering systems used by the Fortune 500.

Get-Content fortune_455_emails.txt | .\Invoke-EmailRecon.ps1 | Export-Csv 455.csv


Raw Table Results:

Email Security Vendor

Count

Proofpoint

141

Self-Hosted

91

Microsoft Exchange Online Protection (EOP)

83

Other/Undetermined

59

Symantec.Cloud

36

Cisco Email Security (Formerly IronPort Cloud)

27

Google

11

Forcepoint (Formerly Websense)

4

Trend Micro

2

FireEye Email Security Cloud

1

 

The results indicate that most are using ProofPoint, Exchange Online Protection, or they are self-hosting their own service of some type.

Comparing the results to Australia, we can see that the US Market is consolidated to a few big players, whereas Australia is reasonably diversified. The significance of this is that malware should theoretically spread slower in Australia, because malware authors would have to work significantly harder to find vulnerabilities across multiple email security solutions if they wanted to infect the majority of the top 250 companies in Australia, whereas in the USA the malware authors just need to find a flaw in ProofPoint and Exchange Online Protection to infect 50% of America’s Fortune 500.

What surprised me was to see ProofPoint has a 6% penetration into the Australian market, compared to 28% in the United States (no surprise since ProofPoint HQ is in the USA).

These results could also be helpful for smaller or mid-size businesses who sometimes look at the decisions made by members of the Fortune 500 as a standard, ex: “good enough for them, good enough for me.”

Universities, think tanks, and research firms like Gartner and Forrester can now take periodic snapshots of this data to determine trends of email security vendors (or IdP federation vendors). Companies could use this data to find out which markets to expand into. And unfortunately Malware authors have most likely already figured out that targeting flaws in ProofPoint and Exchange Online will net them 50% of the Fortune 500.

In the next blog post, I will examine DMARC and IdP adoption trends.

Top 10 Fixes for troubleshooting free/busy between Exchange on-premises and Exchange Online in Office 365

Free/busy often fails to work out-of-the-box after configuring Hybrid Exchange with Office 365. Here are my top ten fixes:

 

  1. Set the sharing policy to match on-premises and cloud.

    First, Connect to Exchange Online Remote Powershell and run get-sharingpolicy

    Then connect to on-premises Exchange Management Shell and run get-sharing policy

    Then make the two match on both sides.

 

Set-SharingPolicy -Identity SharingPolicy01 -Domains ‘contoso.com: CalendarSharingFreeBusySimple’, ‘atlanta.contoso.com: CalendarSharingFreeBusyReviewer’, ‘beijing.contoso.com: CalendarSharingFreeBusyReviewer’

 

  1. Set the organization relationship domains to include all accepted domains on both on-premises and cloud (always requires an IISRESET for it to take effect)
    This script helps identify missing domains in an existing relationship:

     

    if ( (Get-OrganizationRelationship).DomainNames -contains (Get-Mailbox user).PrimarySmtpAddress.Domain) { write-host “The domain was found” -ForegroundColor Green } else { write-host (Get-Mailbox user).PrimarySmtpAddress.Domain “was not found” -ForegroundColor Yellow}

     

    $OrgRel = Get-OrganizationRelationship Contoso

    $OrgRel.DomainNames += “contoso.com”

    Set-OrganizationRelationship $OrgRel.Name -DomainName $OrgRel.DomainNames

     

     

    1. If the autodiscover DNS name is not published in external DNS, and if the client doesn’t want to do that, then manually configure TargetSharingEpr to use the published EWS path

      Get-OrganizationRelationship -Identity “O365 to On-premises – (GUID)” | Set-OrganizationRelationship -TargetSharingEpr https://mail.contoso.com/ews/exchange.asmx

    4) For ‘401 errors’ try disabling the IOC connector in Exchange 2013 to have oAuth fall back to dAuth


    5) Sometimes it’s necessary to set the on-premises EWS virtual directory “WSSecurityAuthentication” value back to defaults (some clients change this if they do load balanced CAS)
    (this is commonly a last resort)

    Need to change WSSecurityAuthentication to False for EWS Virtual directory.

        a.       Set-WebServicesVirtualDirectory “Exch CAS\ews*” –WSSecurityAuthentication $false

        b.      Need to Stop MSExchangeServicesAppPool.

        c.       Need to Start  MSExchangeServicesAppPool.

     

      Need to change WSSecurityAuthentication to True again for EWS Virtual Directory.

        a.       Set-WebServicesVirtualDirectory “Exch CAS\ews*” –WSSecurityAuthentication $True

        b.      Need to Stop MSExchangeServicesAppPool.

        c.       Need to Start  MSExchangeServicesAppPool.

     

      Need to change WSSecurityAuthentication to False for Autodiscover Virtual directory.

        a.       Set-AutodiscoverVirtualDirectory “Exch CAS\Auto*” –WSSecurityAuthentication $false

        b.      Stop MSExchangeAutodiscoverAppPool.

        c.       Start  MSExchangeAutodiscoverAppPool.

     

      Change WSSecurityAuthentication to True again for Autodiscover Virtual Directory.

        a.       Set-AutodiscoverVirtualDirectory “Exch CAS\Auto*” –WSSecurityAuthentication $true

        b.      Stop MSExchangeAutodiscoverAppPool.

        c.       Start  MSExchangeAutodiscoverAppPool.

     

    6) If the Exchange Server is behind a web proxy then it is usually necessary to configure InternetWebProxy Set-ExchangeServer <Server Name> -InternetWebProxy:http://<Proxy Address>:<Proxy Port>

     

    7)  Verify the availability address space and see required SMTP domain with access method.

        Get-AvailabilityAddressSpace (Run this on-prem)

     

    8) Try running diagnostic commands:
    You can also use the Test-FederationTrust (on prem only) and Test-OrganizationRelationship  (run this both on prem and in cloud too)

    And you can also use this website to run tests: https://www.testexchangeconnectivity.com/

    9) Make sure that the cloud user you are searching for has a valid (tenant).mail.onmicrosoft.com alias on their target mailbox (make sure Azure AD Connect is properly replicating that attribute, and/or, that the Exchange Address Policy is not blocking inheritance on that particular user/object).

     

    10) Run these commands to gather diagnostic information:

    Onpremises:

    Start-Transcript

    Get-FederationTrust | fl

    Get-FederatedOrganizationIdentifier | fl

    Get-OrganizationRelationship | fl

    Get-WebServicesVirtualDirectory | Export-Clixml C:\temp\WebVdir.xml

    Get-AutoDiscoverVirtualDirectory | Export-Clixml C:\temp\AutoDVdir.xml

    Get-RemoteMailbox bobc_sync | fl

    Get-Mailbox “on-premises John Doe User” | fl

    Test-FederationTrust -UserIdentity user@domain.com | fl

    Test-FederationTrustCertificate | fl

    Get-IntraOrganizationConnector | fl

    Stop-Transcript

     

    Online:

    Start-Transcript

    Get-FederationTrust | fl

    Get-FederatedOrganizationIdentifier | fl

    Get-OrganizationRelationship | fl

    Get-MailUser “on-premises John Doe User” | fl

    Get-Mailbox “Cloud user” | fl

    Get-IntraOrganizationConnector | fl

    get-OrganizationRelationship | Test-OrganizationRelationship -UserIdentity “cloud user”

    Stop-Transcript

     

     

     

    And when all else fails I reference these two blog articles:

    https://blogs.technet.microsoft.com/exchange/2018/02/06/demystifying-hybrid-freebusy-what-are-the-moving-parts/

    and

    https://blogs.technet.microsoft.com/exchange/2018/03/02/demystifying-hybrid-freebusy-finding-errors-and-troubleshooting/

How to fix Exchange Online Hybrid Outbound Connector 454 4.7.5 Certificate Validation Failure

While recently helping a client setup an Exchange Hybrid, the cloud to on-premises mail flow was failing validation due to 454 4.7.5 Certificate Validation Failure.

The next step was to verify that the TlsCertificateName value was properly set on the send and receive connectors to match the certificate name, following these articles:

https://blogs.technet.microsoft.com/lalitbisht/2017/06/03/mailflow-issue-from-exchange-on-prem-to-office-365/

https://practical365.com/exchange-server/configuring-the-tls-certificate-name-for-exchange-server-receive-connectors/

In this case, the TlsCertificateName was already set correctly to match the certificate name (the Hybrid Exchange Wizard does a good job at setting that correctly).

The next step was to enable Verbose logging on the on-premises receive connector so that we can get a better look at the error.

To save time, I restarted the “Microsoft Exchange Frontend Transport” service so that the logging would take effect sooner.

Then navigating to the log directory can be a bit tricky:

C:\Program Files\Microsoft\Exchange Server\v15\TransportRoles\Logs\FrontEnd\ProtocolLog\SmtpReceive

Opening up the file revealed a very helpful bit of information! The SSL Certificate that Microsoft Office 365 is presenting to the Exchange server for the TLS encrypted email is not a trusted root. How can this be?

 

To cut to the chase, the root cause was that the server had not had windows updates run in a LONG time and therefore was really far behind in its root certificates.

The least disruptive solution was to download the Office certificate chains from Microsoft (here) and install them on the on-premises Exchange Server. Then after restarting the “Microsoft Exchange Frontend Transport” service and waiting a few minutes, the validation was successful.

Passwordless phone sign-in with the Microsoft Authenticator app – not compatible with conditional access require approved client app

This blog post details the effort to enable passwordless phone sign-in to Azure Active Directory using the Microsoft Authenticator App. Last week Microsoft announced this capability on September 26th at the Ignite Conference.

In my environment, I had to first install the Azure AD PowerShell preview module:

Install-Module -Name AzureADPreview -RequiredVersion 2.0.0.114

The first error I got reminded me that I had to run it in an elevated PowerShell window.

The second error I received informed me that there were already existing commands available:

“PackageManagement\Install-Package : The following commands are already available on this system: [Insert a TON of commands] followed by “This module ‘AzureADPreview’ may override the existing commands. If you still want to install this module ‘AzureADPreview’,use -AllowClobber parameter.”

In my case, it errored out because I had previously installed the production Azure AD PowerShell module, so I added the -AllowClobber to the end like this:

Install-Module -Name AzureADPreview -RequiredVersion 2.0.0.114 -AllowClobber

The next thing to do is to connect to Azure AD:

Connect-AzureAD

Then run this command:

New-AzureADPolicy -Type AuthenticatorAppSignInPolicy -Definition ‘{“AuthenticatorAppSignInPolicy”:{“Enabled”:true}}’ -isOrganizationDefault $true -DisplayName AuthenticatorAppSignIn

You can now run a get-AzureADPolicy to see the same information above. This would be a way to check to see if another tenant admin already beat you to the task =)

 

End User Steps

 

End-users need to enable sign-in on their Microsoft Authenticator App as described here: https://docs.microsoft.com/en-us/azure/active-directory/user-help/microsoft-authenticator-app-phone-signin-faq

 

I immediately hit a roadblock where the Authenticator App was ironically blocked by our Conditional Access Policy which requires only approved client apps.

 

Very strange that Microsoft’s own Authenticator app is not an approved client app.

Another tell-tale sign that something was wrong was I had an exclamation point next to the account inside the Authenticator app.

So I then excluded myself from that policy and continued setup. I had to select an option in the Authenticator app to update phone sign-in.

 

This worked and then I was able to test the passwordless sign-in successfully. The web page will give you a number, and then you go back into the authenticator app and you select the number from three options.

If you are wondering why 77 is not in the list of three options below, it’s because I didn’t time the screen shot correctly =)

Therefore, I think Microsoft should update the known issues list to include this problem that existing Conditional Access Policies may block the passwordless sign in from working properly.

I also added a UserVoice request to have Microsoft Authenticator added to the list of approved client apps. Kind of funny that this isn’t approved already, but hey, please vote!

https://feedback.azure.com/forums/169401-azure-active-directory/suggestions/35605771-add-microsoft-authenticator-to-approved-client-app

So unfortunately, because our organization relies upon the ‘require approved client app’ to block unsavory apps, we needed to roll back this change.

Rollback Tenant

Get-AzureADPolicy | Remove-AzureADPolicy

Rollback all enrolled Authenticator apps

I discovered that rolling back the tenant was not enough. I also had to remove my O365 account from inside the Authenticator app on my mobile device. I assume when my account was upgraded to Phone sign-in, it must have altered it beyond repair. So I went into the Authenticator App accounts and removed the account, and then re-enrolled it by going to http://aka.ms/MFASetup. Finally, I was able to get back in.

So now that I have tasted how cool passwordless sign-in, I would really like to use it, but will need to wait until it is compatible with the ‘require approved app’ conditional access feature.

References:

https://docs.microsoft.com/en-us/azure/active-directory/authentication/howto-authentication-phone-sign-in

 

Azure Conditional Access and Azure AD Connect Service Account

If you deploy an Azure Conditional Access policy to require all Windows PC’s to be domain joined, you may find that Azure AD Connect no longer synchronizes.

And during an upgrade to the latest version of Azure AD Connect, you may be prompted with the error message “System.InvalidOperationException: Showing a modal dialog box or form when the application is not running in UserInteractive mode is not a valid operation.”

To resolve this, modify the conditional access policy to exclude the Azure AD Connect Service Account, which can be found by searching for “On-premises directory synchronization service account”

Then create a second conditional access policy that is targeted this same on-prem account with a condition exclusion for all trusted locations, and a block rule for all other access. This effectively creates an IP-Fence that prevents this service account from logging in from anything other than the trusted location.

In Preview: Privileged Access Management for Office 365

Privileged Access Management (PAM) for O365 is a way to restrict access to Office 365 administrative functions by requiring a separate person such as a manager (or someone designated the approver role) to grant access to administrative functions.

PAM is currently a PowerShell-only feature (no graphical user interface… yet) and is limited to Exchange Online at this time. Other workloads such as SharePoint Online are planned in the future. Therefore, it is more or less a proof of concept at this time, because PowerShell is not a skill that most entry-level helpdesk have acquired.

It’s a step in the right direction for sure, as it provides more fine-grained access management than Azure Privileged Identity Management (AzPIM), which gives access to an entire role for a period of time.

Where PAM differs, is that it grants access to perform certain commands only, rather than opening up the entire privileged role to someone.

It’s a nice compliment to AzPIM, but to avoid confusion I feel this should really be part of AzPIM as opposed to a separate O365 E5 feature. Microsoft should be cautious to avoid the appearance of having EMS E5 products compete against O365 E5 products. Case in point, it’s challenging for customers to understand the difference between O365 E5 Cloud App Security versus EMS E5 Cloud App Security. The same product is sold with different feature sets, but why add this confusion? In my opinion, all security elements should be bundled in EMS, and make O365 a pure productivity package. 

The other challenge with O365 PAM, and Azure PIM, is that they do not integrate with the on-premises Windows Server 2016 PAM. So effectively, a customer would have to implement three separate solutions that don’t integrate with each other. This may be a product of Agile software development than anything else. If Microsoft is consistent with what they have done with other products, we should expect to see “Microsoft PAM” which will integrate or replace all three O365 PAM, Azure PIM, and Windows PAM. At that point it will be able to compete strongly against Lieberman (now Bomgar) and/or CyberArk.

Try Office 365 PAM out here: https://docs.microsoft.com/en-us/Office365/Enterprise/privileged-access-management-in-office-365

 

Office 2016 and older clients will not connect to Office 365 after 10/13/2020

Now that Office 2019 is in beta/preview, it may be wise to start planning deployment now because after October 13th 2020, Office 365 ProPlus 2016 and older clients will be actively blocked from connecting to Office 365 services. Only Office 365 ProPlus 2019, or Office perpetual clients within mainstream support can connect to Office 365 services.

https://www.microsoft.com/en-us/microsoft-365/blog/2017/04/20/office-365-proplus-updates/

Actively blocking older clients is a major change in policy compared to the current policy which states “Previous versions of Office, such as Office 2010 and older clients may work with Office 365 with reduced functionality” https://products.office.com/en-US/office-system-requirements

 

 

 

Protecting Smartphones from Ransomware

At the 2018 RSA Conference I attended a session by Kevin McNamee (Director of Nokia’s Threat Intelligence Lab) and learned some valuable things that I would like to share with my blog followers.

From the ransomware samples that Kevin shared, most ransomware targeting Android can be uninstalled by booting the device to safe mode and removing Device Admin priv then uninstalling the app.

In summary the lessons I learned for protecting Android smartphones from Ransomware:

1. Don’t download apps from third party app stores.

2.Make sure “verify apps” is turned on.

3. Keep regular backups of your phone.

4. Consider 3rd party AV for your Android.

Side note: One of the other conference attendees asked Kevin what to do in their situation, where their employees in China are unable to access the Google Play Store, so they have no choice but to use 3rd party app stores. Kevin suggested that they rely upon 3rd party AV and employee security awareness training.

What about Apple iOS?

According to Kevin, AV is not necessary for iPhones because Apple doesn’t give AV vendors an API to do much good. He felt that the level of isolation in iOS is sufficient.

Not completely satisfied with this, I approached Kevin in the hallway and asked him about Pegasus Spyware –commercially available spyware sold by a startup company called the NSO Group, targeting iPhones (and Google/Blackberry) that was sold to governments. LookOut software participated in the discovery of this software which used three zero day exploits dubbed Trident (since then it has been patched in iOS 9.3.5). I asked Kevin, “Isn’t Trident an example of why we should advocate for 3rd party smartphone security software, such as LookOut?” My concern is that there could be more zero day exploits? The point I tried to make is that if you had LookOut software (or software like it), then wouldn’t you be better off? Kevin was skeptical that these vendors are actually doing much good.

For what it is worth, Lookout is still the only software that can detect Trident (according to Trident). Here is more about their discovery and how their software protected against it: https://www.lookout.com/trident-pegasus-enterprise-discovery

 

My recommendations:

If you are the one responsible for purchasing decisions of “company-owned smartphones” for your company, my recommendation is to avoid purchasing Android and purchase iPhones instead, unless you can mandate good AV installed on the Android. This is because attackers have a higher cost to find zero-day exploits like Trident. Kevin also mentioned that an attacker’s could also target iOS with social engineering techniques to get into the target’s iCloud account, and then perhaps remotely locking the phone until the ransom is paid. Kevin said even in that scenario you may be able to work with Apple to get into the account.

Microsoft has improved their Intune Mobile Device Management to support 3rd party connectors that can provide conditional access, so that only clean devices can access corporate resources such as Office 365 Exchange and SharePoint.

“Intune Mobile Threat Defense connectors allow you to leverage your chosen Mobile Threat Defense vendor as a source of information for your compliance policies and conditional access rules. This allows IT administrators to add a layer of protection to their corporate resources such as Exchange and Sharepoint, specifically from compromised mobile devices.”

There are currently four vendors supported to integrate with Intune:

Lookout

Skycure

Check Point SandBlast Mobile

Zimperium

When I looked at them, they looked very similar to me. I have not formally evaluated them but I will be speaking with each vendor since they are here at #RSAC 2018

Attack Simulator for Office 365

Microsoft has released Attack Simulator [See full GA Announcement 4/27/2018 here] to allow Office 365 Global Administrators to simulate phishing campaigns and other attack simulations.

The obvious value is finding out which users are most susceptible to phishing attacks so that you can educate them before an actual attacker exploits them.

Prerequisites

  • Your organization’s email is hosted in Exchange Online (Attack simulator is not available for on-premises email servers)
  • You have an E5 license, or have signed up for an E5 trial license (here), or an Office 365 Threat Intelligence Trial (here)
  • You have the security administrator role or Global Administrator role assigned to you
  • You have multi-factor authentication enabled (make sure to first read the MFA prerequisites here, such as enabling oAuth via powershell)

Getting Started

To access Attack Simulator, in the Security & Compliance Center, choose Threat management > Attack simulator. Or you can browse to it directly here:

https://protection.office.com/#/attacksimulator

There are currently three attacks offered by Attack Simulator:

  1. Display name spear-phishing attack
  2. Brute Force password attack
  3. Password spray attack

In this blog post we will quickly cover the first simulation. Feel free to click on the documentation link in the reference table below to read about the other two attack simultaneous.

Display name spear-phishing attack

One of the more common and successful phishing methods is to spoof the Display Name field in Outlook. This is very effective because Sender Policy Framework (SPF) only protects the RFC 5321.Mail From field, and does not protect against spoofing of the Display Name. Only Domain-based Message Authentication, Reporting & Conformance (“DMARC” – RFC 7489) protects against the Display Name field (RFC 5322.From Field). However, since very few organizations have implemented DMARC, then this simulated phishing attack is very effective.

Carrying out the phishing simulation is a straight-forward wizard in the documentation found (here). Basically you enter the email address that you want to spoof and the targeted users that you want to send the fake email to. You can pick from a few pre-built templates, then you can do some customization of the email that would be sent out. After running the campaign, you can monitor to see which users clicked on the link, and which users went a step further and gave away their credentials.

Behind the scenes

Penetration testers may be tempted to try Attack Simulator against other tenants, but Microsoft has thought of that and restricts Attack Simulator to only attack its own tenant.

Another temptation would be to use Attack Simulator to test the effectiveness of your anti-spam technologies (ATP or EOP). However, Attack Simulator is designed to bypass EOP and ATP, which you can confirm by looking at the Message Trace in Exchange Online control panel (http://outlook.com/ecp), as you won’t find any traces of Attack Simulator in the message trace, and therefore it is apparent that it bypasses all EOP and ATP protection rules. You wouldn’t want EOP or ATP blocking your attempt to phish your users, right? Perhaps in the future Microsoft could add a toggle that allows the simulated phishing campaign to be filtered by EOP/ATP to verify that those technologies are able to successfully block the phishing campaign.

How does this compare to other Phishing Simulators?

Other phishing simulators such as KnowBe4 or PhishMe have been around a lot longer, obviously, but Attack Simulator is great for customers who maybe already own the E5 license and want to phish their users at no added cost. If you only have E3 then you could purchase “Threat Intelligence” as an add-on license on top of E3 in order to get the Attack Simulator feature. However, there is another recently added feature included in the Advanced Threat Protection (ATP) license called ATP Anti-Phishing Policies which you would also get in the E5 license and therefore I feel the best value is to get the E5 rather than trying to purchase separate add-ons. I wrote a little bit about the new Anti-Phishing solution in my recent post where I wrote about the top 15 things to do before and after a phishing attack in Office 365. Basically, the new Anti-Phishing Policy can send items to quarantine if any part of the email address has been modified to bypass DMARC. For example, while DMARC protects the exact spelling of an impersonated CEO, it does not protect against a slight variation of a CEO’s address. Like Joe.Ceo@Contoso.com spelled with a zero instead of an alphabetic O, like Joe.Ceo@C0ntoso.com. In those cases, the new Anti-phishing policy can be configured to send those emails to quarantine, or redirect them to a security team, or other actions.

Need help?

Patriot Consulting provides assistance with deploying Microsoft Security solutions. We start with a free consultation to help you understand your current Microsoft licensing level, and we help you deploy the security solutions that you may already own inside your Microsoft licenses. Then we can help you pilot additional security solutions from Microsoft.

Why Patriot?

We are a Microsoft Gold Enterprise Mobility + Security Partner and have helped hundreds of companies deploy Microsoft security solutions. We focus 100% exclusively on Microsoft Cloud technologies and believe in “do one thing and do it well.” We participate in the Microsoft Partner Seller Program, and we are a Managed Microsoft Partner, which gives us access to the latest training and roadmap. As a member of the Microsoft Security Council, we have direct access to the Microsoft Product Group that develops the software.

References: